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To a solution of phenylmethanol (2.248 g, 20.79 mmol) in THF (100 mL), was added NaH (60% w/w) (0.914 g, 22.86 mmol) at 0C. The reaction mixture was stirred at 0C for 4 hr. 4-bromo-2- chloropyridine (2 g, 10.39 mmol) in THF (50 mL) was added dropwise into the reaction mixture at 0 C. The reaction mixture was stirred at 25C for overnight. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was washed with saturated brine (100 mL), dried over sodium sulphate and evaporated in vacuo to give the crude product. The crude product was purified by Combi-Flash chromatography on a silica column (24g) and eluted with EtOAc/petroleum (0-100% over 10 min, 100% over 5 min). Appropriate fractions were evaporated to give the title compound (1.272 g, 4.82 mmol, 46.3 % yield) as a white oil. LCMS: MH+ =264/266
0.71 g
(1) 0.37 g of sodium hydride was added to a mixed solution comprising 1.1 g of benzyl alcohol and 3 mL of tetrahydrofuran while cooling with an ice bath, followed by stirring at room temperature for 10 minutes. A mixed solution comprising 0.60 g of 4- bromo-2-chloropyridine and 1 mL of tetrahydrofuran, was added to the reaction solution, followed by heating and refluxing for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n- heptane/ethyl acetate=10/1) to obtain 0.71 g of oily 2-(benzyloxy)-4-bromopyridine.
3-(2-chloro-4-pyridinyl)tetrahydro-3-furanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1 g
To a stirring solution of 4-bromo-2-chloropyridine (1.154 mL, 10.39 mmol) in diethyl ether (40 mL) at -70 °C was added n-butyllithium, 2.5 M solution in hexanes (4.57 mL, 11.43 mmol) at a rate that did not exceed an internal temperature of -65 °C. After stirring the resulting suspension for 5 min a solution of 3 -oxotetrahydrofuran (CombiBlocks, Inc., 0.984 g, 11.43 mmol) in diethyl ether (4 mL) was added at a rate that did not exceed an internal temperature of 60 °C. The suspension was stirred for 15 min then warmed to -50 °C at which point it was quenched with saturated NH4C1 (20 mL). To the reaction was added water (20 mL). The separated organic was then dried onto silica gel (20 g) under reduced pressure. The product was then purified by silica gel chromatography (80 g) eluting products with 0 to 5percent gradient of MeOH/CH2Cl2 to afford 3-(2-chloro-4-pyridinyl)tetrahydro-3-furanol (1.0 g) as colorless oil (mixture of 2 enantiomers).
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