反应详情

To a solution of triisopropylsilanethiol (1.75 mL, 8.05 mmoles) and (4-bromophenyl)(phenyl)methanol from example 67 step 2 (3.5, 8.05 mmoles) in 16 mL of DMF was added sodium hydride as a 60% emulsion in oil (386 mg, 9.66 mmoles). After the exotherm has passed, 1.65 mL (10 mmole) of methyl 2-bromo-4-methylpentanoate was added followed by 12 mL of a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran. After stirring overnight, the reaction was diluted with diethyl ether (200 mL) and washed twice with 0.1 N HCl, twice with water and once with brine. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The oil as purified by flash chromatography (9:1 hexanes to ethyl acetate) to give the title ester.

1. washwashed twice with 0.1 N HCl, twice with water and once with brine
2. dry with materialThe organic phase was dried over magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe oil as purified by flash chromatography (9:1 hexanes to ethyl acetate)