Allyl bromide → HCID 14297067, compound

Temperature

0 °C

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.).

1. stirringThe resulting mixture was stirred for 16 hrs at 23° C.
2. custombefore being quenched by addition of a saturated aqueous ammonium chloride solution
3. extractionThe organic layer was extracted with trichloromethane
4. washwashed with saturated aqueous sodium chloride
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. distillationDistillation at atmospheric pressure

ORD record

ord-ed6b1f76170e4ba59d1bfe844a2a619e

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501980B2