Allyl chloride → HCID 69380150, compound

Temperature

40 °C

Mg metal turnings (0.33 g, 13.7 mmol) were placed in a clean, dry round bottom flask and flame-dried under vacuum. Freshly-distilled THF (2.5 mL) was added to the flask, and the contents were heated to reflux. The mixture was cooled to 40° C., and a solution of allyl chloride (0.75 mL, 0.70 g, 9.1 mmol) in THF (2.5 mL) was added dropwise over a 30 minute period. The resulting Grignard solution was held at 40° C. for an additional 20 minutes. The mixture was then cooled to −42° C. (dry ice/chlorobenzene bath), and a solution of the enone Compound 3 (0.5 g, 3 mmol) in THF (2.5 mL) was added dropwise. After 5 minutes, the cooling bath was removed, and the reaction was stirred for 1.5 hours as it warmed to room temperature. The mixture was then decanted into ice-cold 0.1 N HCl (50 mL) and extracted with ether. The combined organic fractions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Column chromatography (with 90:10/Hexane: EtOAc) provided Compound 4b (0.62 g, 98% yield) as a colorless liquid.

1. customdry round bottom flask
2. customflame-dried under vacuum
3. additionFreshly-distilled THF (2.5 mL) was added to the flask
4. temperaturethe contents were heated to reflux
5. waitAfter 5 minutes
6. customthe cooling bath was removed
7. temperaturewarmed to room temperature
8. customThe mixture was then decanted into ice-cold 0.1 N HCl (50 mL)
9. extractionextracted with ether
10. washThe combined organic fractions were washed with water and brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-3c48ddc5c5e34e0ba85b9651550d5702

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112700B1