Allyl bromide → (S)-4-(allyloxy)pent-1-ene

Temperature

0 °C

To a suspension of sodium hydride (21 g, 34 mmol) in N,N-dimetylformamide (100 mL) was dropwise added (S)-pent-4-en-2-ol (10 g, 116 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. After that, allyl bromide (14.0 g, 116.2 mmol) was dropwise added to the mixture at 0° C. The resultant mixture was stirred at 0° C. for another 3 h, and the mixture was quenched by saturate ammonium chloride solution (500 mL). The aqueous layer was extracted with tert-butyl methyl ether (200 mL×3), and the combined organic layers were washed with water (100 mL×3) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford (S)-4-(allyloxy)pent-1-ene (˜20 ml tert-butyl methyl ether solution), which was used in the next step without further purification.

1. customat 0° C
2. customthe mixture was quenched
3. concentrationby saturate ammonium chloride solution (500 mL)
4. extractionThe aqueous layer was extracted with tert-butyl methyl ether (200 mL×3)
5. washthe combined organic layers were washed with water (100 mL×3) and brine (100 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-e096234f78734783b5294987df680f9b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2