Oct-6-en-2-one → HCID 14127272, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.0 g of (1S,6R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one, the compound of formula (XXXIX), prepared as shown in Preparation 22, is dissolved in 120 ml of methanol and treated at 0° C. with 1.2 g of sodium borohydride, and the mixture is stirred at 25° C. for 1 hour. The solvent is removed under reduced pressure and the residue partitioned between methylene chloride and water. The extract is dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure. The residue is recrystallized from hexane to give (1S,6R,7R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-ol, [α]D =+214.4°, (C=0.5, CHCl3).

Provenance & Evidence