Allyl bromide → HCID 68003986, compound

Participants

Reaction Conditions

Reaction Steps

In a dry 3-necked flask flushed with argon containing a solution of 11 (6.86 g, 19.05 mmol) in THF (40 mL) at 0° C. was added a 1.3 M THF solution of isopropyl magnesium chloride lithium chloride complex (19.1 mL, 24.8 mmol) over 10 min. After 10 additional minutes of stirring at 0° C., CuI (0.73 g, 3.81 mmol) was added, the mixture was stirred for 10 minutes at 0° C. and then a solution of allyl bromide (3.3 mL, 38.1 mmol) in THF (4.0 mL) was added at 0° C. over 10 min. After further stirring for 1 h at 0° C., the reaction was quenched with 10% citric acid and extracted with ethyl acetate (100 mL×2). The organic layers were combined which was washed with brine, dried over Na2SO4, and concentrated. The obtained residue was chromatographed on silica gel eluted with hexane and 10% ethyl acetate in hexanes to afford 4.22 g of 12 (69%) as a colorless oil which was used directly for the next step. LC/MS (M+1) 322.

Provenance & Evidence