Tetrahydrofuran → Benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:13][CH2:12]1.C1C[O:31]CC1>>[OH:31][CH:17]([CH:14]1[CH2:13][CH2:12][O:11][CH2:16][CH2:15]1)[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
A 1.0 M sodium bistrimethylsilylamide solution in THF (13.0 ml, 12.82 mmol) was added to anhydrous THF (15 ml), and the mixture was cooled to −78° C. A solution of benzyl 2-(tetrahydro-2H-pyran-4-yl)acetate (2.5 g, 10.68 mmol) in anhydrous THF (20 ml) was added dropwise to the mixture over 30 min. The mixture was stirred at −78° C. for one hr, and a solution of n-benzyl-benzenesulfonyloxaziridine (3.35 g, 12.82 mmol) in anhydrous THF (30 ml) was added dropwise thereto over one hr. The mixture was stirred at −78° C. for one hr, was quenched with saturated ammonium chloride, and was extracted with ether. The organic layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2) to give the title compound as an oil (2.1 g, yield 78%).