Hexane → Zifrosilone

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-trimethylsilyl-bromobenzene (7.62 g, 33.3 mmol) in diethyl ether (35 ml) was added at 0° C. 1.5M n-butyllithium in hexane (22.2 ml, 33.3 mmol) over 10 min. Then the mixture was allowed to react 15 min at room temperature, cooled to -78° C. and ethyltrifluoroacetate (14.2 g, 100 mmol) was added over 5 min. Then the mixture was allowed to react 15 min at -78° C., the cooling bath was removed and when the temperature rose to 0° C. 3N HCl (35 ml) was added dropwise. The organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated. Chromatography (silica gel, cyclohexane/diethyl ether: 90/10) followed by distillation under reduced pressure afforded the expected compound as a colorless oil (4.32 g, 53% yield), b.p. 120° C., Rf: 0.28 (cyclohexane/diethyl ether: 95/5).

Provenance & Evidence