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CAS No. : | 7748-36-9 | MDL No. : | MFCD09056790 |
Formula : | C3H6O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | QMLWSAXEQSBAAQ-UHFFFAOYSA-N |
M.W : | 74.08 | Pubchem ID : | 9942117 |
Synonyms : |
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Signal Word: | Danger | Class: | |
Precautionary Statements: | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H318-H335 | Packing Group: | |
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 |
---|---|---|
86% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18.0h; | Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 3- bromo-5-methylphenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) and triphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10percent) to give the title compound (218 mg, 0.827 mmol, 86percent) as a colorless oil |
86% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18.0h; | Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 3- bromo-5-methylphenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) and triphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1 N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10percent) to give the title compound (218 mg, 0.827 mmol, 86percent) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | To a solution of oxetan-3-ol (0.273 mL, 4.14 mmol) in dry DMF (5 mL) was added sodium hydride (60% in mineral oil, 265.5 mg, 5.53 mmol), and the mixture was stirred at r.t. for about 1 h. 5-(Chloromethyl)-l,3-dimethyl-lH-pyrazole (400 mg, 2.76 mmol) in DMF (5 mL) was added and the reaction mixture was stirred for 16 h at r.t. After removal of DMF under vacuum, the residue was dissolved in DCM (50 mL) and water (20 mL). The aqueous layer was extracted with DCM and the combined organic extracts were washed with brine, then dried over Na2S04 and evaporated to dryness. The crude residue was purified by column chromatography, with a gradient of 25-100%) EtOAc in heptane, to afford the title compound (349 mg, 69%). Method B HPLC-MS: MH+ mlz 183, RT 1.09 minutes (100%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18h; | Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 2- bromo-5-chlorophenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) andtriphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1 N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10%) to give the title compound (208 mg, 0.789 mmol, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In toluene; for 12h;Reflux; Dean-Stark; | To a solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (1 g, 7.03 mmol, 1.2 eq.) in toluene (5 ml) was added oxetan-3-ol (0.37 ml, 5.87 mmol, 1 eq). The resultant mixture was refluxed using a Dean-Stark trap for 12 hours, cooled to RT and concentrated. The resulting residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:3) as eluent to afford the title compound as a light-yellow oil (0.52 g, 44%). 1H-NMR (300 MHz, CDCl3) δ = 5.50 (p, J = 5.8 Hz, 1 H), 4.99-4.81 (m, 2H), 4.66 (dd, J = 7.8, 5.8 Hz, 2H), 3.63 (s, 2H), 2.02 (tt, J = 7.8, 4.5 Hz, 1 H), 1.17-1.08 (m, 2H), 1.05-0.93 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4 mg | With sodium carbonate; In acetonitrile; at 100℃; for 1h;Microwave irradiation; | To the reaction flask was added 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]benzamide (60 mg), Na2CO3 (250mg), acetonitrile (10ml) and 3-hydroxyoxetane (50 mg). the reaction was heated in a microwave at 100C for 1 hour, and the product was subjected to preparative HPLC to give Compound 6 (4 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.41% | To a solution ofNaH (1.97 g, 49.14 mmol, 60% purity) in DMF (25 mL) was added oxetan-3-ol (2.37 g, 31.94 mmol) at 0 C and the mixture was stirred for 0.5 h. To the mixture was added a solution of <strong>[327056-62-2]5-fluoropicolinonitrile</strong> (3 g, 24.57 mmol) in DMF (15 mL) at 0 C and stirred at 0 C for 0.5 h. The reaction mixture was poured into saturated NtUCl at 0 C and the aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography to give 5-(oxetan-3-yloxy)picolinonitrile (4 g, 22.71 mmol, 92.41% yield). |
[ 86087-23-2 ]
(S)-(+)-3-Hydroxytetrahydrofuran
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