Potassium Carbonate → (2R,3R)-2-(benzyloxymethyl)-3-(2-chlorophenyl)oxirane

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-1-(3-(benzyloxy)prop-1-enyl)-2-chlorobenzene (Preparation example 367, 4.16 g, 18.58 mmole) and 1,2;4,5-di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose (5.76 g, 22.30 mmole) in DME-DMM (3:1, v/v) (185 mL) was added buffer (0.2M K2CO3—AcOH in 4×10-4 aq. EDTA, buffer pH=8.0) (185 mL) and Bu4NHSO4 (0.26 g, 0.75 mmole). After the mixture was cooled to 0° C., a solution of Oxone (15.76 g, 25.64 mmole) in 4×10-4 aq. EDTA (100 mL) and a solution of K2CO3 (13.6 g, 98.47 mmole) in 4×10-4 aq. EDTA (100 mL) were added dropwise separately over a period of 3.5 hr via a syringe pump at 0° C. The reaction mixture was stirred for 14 hr at 0° C. The reaction mixture was quenched with H2O then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O then dried over MgSO4 and evaporated under reduced pressure The crude compound was purified by silica ge column to produce the title compound (2.9 g, 56%).

Provenance & Evidence