Allyl bromide → HCID 14297067, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% in oil, 2.76 g, 68.3 mmol) was added to a solution of 3-pentanol (4 g, 45.5 mmol) in tetrahydrofuran (20 mL) at 0° C. under argon atmosphere. The reaction mixture was stirred for 10 min at 0° C. followed by addition of allyl bromide (8.2 g, 68.3 mmol) and tetrabutylammonium iodide (60 mg, 0.016 mmol). The resulting mixture was stirred for 16 hrs at 23° C. before being quenched by addition of a saturated aqueous ammonium chloride solution. The organic layer was extracted with trichloromethane, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. Distillation at atmospheric pressure yielded 3-(allyloxy)pentane (compound S1, 4.8 g, yield 82%, boiling point 115° C. to 120° C.)

Provenance & Evidence