Hexane → HCID 19000627, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of S-methyl-N-methyl-S-phenyl-sulfoximine (2.04 g, 12 mmol) and triphenylmethane (5 mg) in dry THF (20mL) is added dropwise to a solution of n-butyllithium (1.6 mol) in hexane (7.5 mL, 12 mmol) at 0° C. A solution of phenylthio-methyl cyclopent-1-enyl ketone (2.18 g, 10mmol) in dry THF (10 mL) is then added slowly during a period of 10 minutes. After stirring at 0° C. for 30 minutes, the mixture is poured into a 5% ammonium chloride aqueous solution (50 mL) and extracted with dichloromethane (40 mL×3). The combined extracts are washed with H2O, dried (Na2SO4), and evaporated in vacuo to dryness. The thin layer chromatography (TLC, SiO2, toluene/EtOAc, 9:1 v/v) of the mixture showed that it contains a mixture of diastereomers in a syrup, 2.70 g (70%) (Rf=0.43 and 0.37), which are isolated by liquid chromatography (SiO2, touene/EtOAc, 9:1 v/v) and used directly in the next step without further separation.

Provenance & Evidence