Cyclohexene oxide → HCID 18653088, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.24 g (0.1 35 mol) of magnesium and 20 ml of tetrahydrofuran was charged into a three-necked flask of 300 ml and stirred. Then, a solution of 35.6 g of o-benzyloxyphenylbromide in 80 ml of tetrahydrofuran was added dropwise at a temperature of 60° C. or less. After the dropping was stopped, the mixture was cooled to -30° C., 0.65 g of cuprous chloride was added, and the mixture was stirred for 10 minutes. To the mixture, a solution of 13.3 g (0.135 mol ) of cyclohexene oxide in 15 ml tetrahydrofuran was added dropwise at -30° C. After the dropping was stopped. The temperature was raised to 0° C., and the mixture was stirred for three hours at 0° C. After the temperature was raised to room temperature, the mixture was charged into a separatory funnel and extracted with 600 ml of methylene chloride, and the organic layer was washed with 600 ml of saturated ammonium sulfate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled away under reduced pressure. The concentrate was distilled under reduced pressure to obtain 26.5 g (0,094 mol) of (±)-trans-2-(2-benzyloxyphenyl)-1-cyclohexanol.

Provenance & Evidence