Benzyl Bromide → HCID 69046728, compound

Participants

Reaction Steps

To a suspension of 3.2 g (133 mmol) sodium hydride (freed from paraffin) in 105 ml ice cold abs. tetrahydrofuran was added 6.2 g (39.5 mmol) (S)-dec-9-ene-2-ol under argon. After stirring for 2 h, 470 mg (1.3 mmol) tetra-n-butyl ammonium iodide were added, followed by dropwise addition of 13.5 g (9.4 ml, 78.9 mmol) benzyl bromide, while stirring was continued for 12 h. Subsequently, 50 ml saturated aqueous ammonium chloride solution were added at 0° C. followed by 50 ml hexane. The aqueous layer was separated and extracted four times with 100 ml of a 1:4 mixture of ethyl acetate/hexane. The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. Flash chromatography (5% ethyl acetate in hexane furnished 9.7 g (39.4 mmol, 100%) (S)-2-benzyloxydec-9-ene.

Provenance & Evidence