Allyl bromide → HCID 86762140, compound

Temperature

0 °C

2,4-pentanedione (4.11 mL, 39.9 mmol) was dissolved in anhydrous THF (120 mL) and cooled to 0° C. using an ice-water bath. To the stirred THF solution, 2.2 equivalent of 2.0 M LDA (44 mL, 87.8 mmol) was slowly added. After addition was complete, the mixture was stirred at 0° C. for 20 min under argon atmosphere. Allyl bromide (3.46 mL, 39.9 mmol) was then added to the resulting pale red solution at 0° C. under argon. After removing of ice-water bath, the resulting reaction was allowed to stir for 20 min at room temperature before being quenched by saturated aqueous 1 M of HCl (aq). The reaction mixture was extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with brine, water (3×50 mL), dried over MgSO4. After filtration, the solution was concentrated, and the residue was purified by chromatography using 9:1 ratio of n-hexane:EtOAc. The product, 3, was isolated as a pale yellow oil, 1.21 g (22% yield).

1. additionAfter addition
2. customAfter removing of ice-water bath
3. customthe resulting reaction
4. stirringto stir for 20 min at room temperature
5. custombefore being quenched by saturated aqueous 1 M of HCl (aq)
6. extractionThe reaction mixture was extracted with EtOAc (2×50 mL)
7. washThe combined EtOAc extracts were washed with brine, water (3×50 mL)
8. dry with materialdried over MgSO4
9. filtrationAfter filtration
10. concentrationthe solution was concentrated
11. customthe residue was purified by chromatography
12. customThe product, 3, was isolated as a pale yellow oil, 1.21 g (22% yield)

ORD record

ord-fb9c6db5c014494eb3cbb741ba4bb6f5

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08597803B2