反应详情

A solution of 1.98 g of aldehyde 7 in 15 mL of tetrahydrofuran is cooled to 10° C. and is treated with the Grignard reagent prepared by treating 1.23 g of ((S)-2-bromomethyl-3-methylbutoxymethyl)-benzene with 0.12 g of magnesium in diethylether containing 0.043 g of 1,2-dibromoethane at 45° C. The reaction is stirred for 90 minutes at room temperature, then 20 mL of a 25% aqueous solution of ammonium chloride is added, followed by addition of 20 mL of tert-butylmethyl ether. The organic phase is separated and washed twice with 20 mL of water. The organic phase is concentrated in vacuum to give the crude alcohol 8 as an oil. Purification on silica-gel delivers e.g. 0.97 g of pure 8. A negative [a]d is found at c=1, CHCl3. M++H=628, M++H+Na=650.

1. customprepared
2. customThe organic phase is separated
3. washwashed twice with 20 mL of water
4. concentrationThe organic phase is concentrated in vacuum