Water → HCID 69049493, compound

Participants

Reaction Conditions

Reaction Steps

A vigorously stirred solution of 6.0 g (24.3 mmol) (S)-2-benzyloxydec-9-ene in 300 ml of a 1:1 mixture of water and tert-butanol was cooled to −10° C. After addition of 29.2 g AD-Mix β (i.e. 1.2 g per mmol alkene) the mixture was stirred at 4° C. for 40 h. Subsequently, 30.0 g (158 mmol) sodium disulfite were added, and the mixture was stirred at 20° C. for another hour. The brownish suspension was extracted three times with 250 ml ethyl acetate. The organic layers were combined, dried over magnesium sulphate, and concentrated in vacuo. Flash chromatography (ethyl acetate and hexane 1:1) furnished 4.2 g (15 mmol, 62%) (2R,9S)-9-benzyloxydecan-1,2-diol as a colorless oil.

Provenance & Evidence