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CAS No. : | 1086378-35-9 | MDL No. : | MFCD11042246 |
Formula : | C9H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SVWYSYMOKICPBK-UHFFFAOYSA-N |
M.W : | 177.16 | Pubchem ID : | 19771047 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.2% | With toluene-4-sulfonic acid; for 0.5h;Inert atmosphere; Reflux; | General procedure: The compound obtained in Example 32-1 (400 mg, 3.20 mmol) triethyl orthoformate (3.2 ml, 19.2 mmol) in solution,para-tosylic acid monohydrate(30 mg, 0.16 mmol) was added dropwise. Under an argon atmosphere, followed by stirring for 30 minutes under reflux conditions, it was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (232 mg, 54%) |
Example XV Methyl 2-benzoxazole-7-carboxylate STR34 5.8 ml of CCl4 in 5 ml of acetonitrile were added to 30 mmol of the compound from Example XIV, 30 mmol of benzoic acid, 50 mmol of triphenylphosphine and 120 mmol of triethylamine in 100 ml of acetonitrile at 3 C. under argon in the course of 15 min and the mixture was stirred at room temperature for 20 hours and concentrated, diethyl ether was added to the residue, the solid was filtered off with suction, the filtrate was concentrated and the residue was separated on silica gel. M.p.: 77 C. (white needles) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) iodide; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; for 20.0h;Inert atmosphere; Reflux; | General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With ytterbium(III) triflate; In toluene; at 100℃; for 1.0h;Microwave irradiation; | Methyl 3-amino-2-hydroxybenzoate (1.69 g, 10.13 mmol) was suspended in toluene (2 mL) in a microwave vial. HC(OEt)3 (1.80 g, 12.15 mmol) and Yb(OTf)3 (0.003 g, 0.005 mmol) was added and the reaction was heated at 100 C for 1 hour in the microwave. The reaction mixture was evaporated and purified by flash chromatography (petroleum ether/EtOAc 4:1) to give the title compound (1.63 g, 91%) as pale yellow crystals. mp. 116 - 118 C (Litt9. 77 C). 1H NMR (300 MHz, CDCl3) delta 8.21 (s, 1H), 8.04 (dd, J = 7.8, 1.2 Hz, 1H), 7.99 (dd, J = 8.0, 1.2 Hz, 1H), 7.44 (dd, J = 8.0, 7.8 Hz), 3.76 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 180.9, 164.4, 153.4, 141.4, 128.0, 125.6, 124.5, 115.4, 52.6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 0.5h; | Methyl benzo[d]oxazole-7-carboxylate (1.57 g, 8.86 mmol) was dissolved in dry THF (50 mL) and there was added a 1.0M solution of LiAlH4 in THF (5mL, 5 mmol). The reaction was stirred at room temperature for 30 minutes at which point TLC indicated full conversion. The reaction was quenched by addition of water (50 mL) and there was added saturated aqueous Rochelle salt (50 mL) and Et2O (50 mL). The reaction was stirred vigorously for 15 minutes and then transferred to a separatory funnel. The organic layer was isolate and the aqueous layer was extracted with Et2O (2 × 100 mL). The combined organic layers were washed with saturated aqueous Rochelle salt (50 mL) and water (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (petroleum ether/EtOAc 3:1) to give the title compound (0.823 g, 62%) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.07 (s, 1H), 7.69 (dd, J = 7.7, 1.3 Hz, 1H), 7.40 (dd, J = 7.7, 1.3 Hz, 1H), 7.33 (t, J = 7.7 Hz), 5.00 (s, 2H), 2.51 (br s, 1H). 13C NMR (75 MHz, CDCl3) delta 153.4, 145.4, 140.0, 124.8, 124.7, 124.4, 119.9, 60.3 |
14.5% | With sodium tetrahydroborate; ethanol; calcium chloride; In tetrahydrofuran; at 20℃; for 2.0h;Cooling with ice; | The compound obtained in Example 51-2 (1.221 g, 6.89 mmol) and THF (24 ml), was dissolved in ethanol (24 ml), cooled with ice. Thereto calcium chloride (1.529 g, 13.78 mmol), sodium borohydride (1.043 g, 27.56 mmol) was stirred at room temperature for 2 hours added. After the reaction was extracted with ethyl acetate by adding 1 mol / l hydrochloric acid. It was washed with a saturated aqueous sodium bicarbonate solution. Dried with magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (SNAP ULTRA 25 g, hexane / ethyl acetate) to give the title compound (149 mg, 14.5%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In tetrahydrofuran; 2-methyltetrahydrofuran; at 0 - 20℃; | A solution of <strong>[1086378-35-9]methyl benzo[d]oxazole-7-carboxylate</strong> (300 mg, 1.7 mmol) in THF (5 mL) was cooled down to 0C and methyl magnesium bromide 3.2M in 2-Me-THF (3.0 equiv., 5.1 mmol) was added dropwise. The mixture was allowed to warm-up to room temperature and quenched with saturated solution of NH4Cl. The resulting mixture was extracted 3 times with EtOAc and the organic solutions were washed with brine, dried with Na2SO4 and concentrated to dryness. The crude was purified by column chromatography on silica gel using DCM:EtOAc (95:5) as mobile phase to give 2-(benzo[d]oxazol-7-yl)propan-2-ol (110 mg, 37%). UPLC-MS (Acidic Method, 2 min): rt 0.78 min, m/z 178.0 [M+H]+ |
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