反应详情

Sodium borohydride (0.59 g, 15.6 mmol) was added portion wise to a stirred solution of 1,1-dimethylethyl 2-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-5-(4-iodophenyl)-3-oxopentanoate (7.55 g, 14.2 mmol) in methanol (100 mL) at 0° C. under nitrogen. On completion of addition stirring was continued for 1.5 h then the reaction was quenched with saturated aqueous ammonium chloride solution (100 mL). The resulting mixture was extracted with diethyl ether (3×200 mL) then the organic layers were combined, washed with brine (100 mL), dried (sodium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (25% to 50% diethyl ether:cyclohexane) to give the title compound (5.14 g, 68%) as a colourless oil which was a mixture of diastereomers.

1. additionOn completion of addition
2. customthe reaction was quenched with saturated aqueous ammonium chloride solution (100 mL)
3. extractionThe resulting mixture was extracted with diethyl ether (3×200 mL)
4. washwashed with brine (100 mL)
5. dry with materialdried (sodium sulfate)
6. customthe solvent evaporated
7. customThe residue was chromatographed on silica gel (25% to 50% diethyl ether:cyclohexane)