t-Butylammonium fluoride → (S)-3-Isopropenyl-cyclopent-2-enol

Participants

Reaction Steps

A solution of compound (6a) (402.8 mg; 1.689 mmol) in THF (34 mL) was cooled to 0° C. and treated with 1.0 M tert-Butylammonium floride (2.55 mL, 2.55 mmol). The next 3½ hours the reaction mixture was stirred at room temperature and then quenched with saturated aqueous NH4Cl. The resulting solution was extracted with DCM (3×) and AcOEt (1×), dried (Na2SO4) and concentrated in vacuo. Purification by chromatography (pentane/ether 3/1 to 2/1) provided 190.4 mg of compound (7a) as clear yellow oil with 95% yield.

Provenance & Evidence