Water → HCID 178489287, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.94 g (5.0 mmol) of 30 in 20 mL of THF, 4.0 mL (10.0 mmol) of 2.5 M nBuLi in hexanes was added at −80° C. This mixture was stirred at this temperature for 1 hr, then cooled to −100° C., and 10.8 mL (10.8 mmol) of 1.0 M ZnCl2 in THF was added. The resulting mixture was slowly warmed to ambient temperature, stirred for 30 min, and then 2.82 g (15.0 mmol) of 2-bromoanisole and 0.14 g (0.25 mmol) of Pd(PtBu3)2 was added. This mixture was refluxed for 8 hr, then 5 mL of water was added. The resulting mixture was passed through short layer of silica gel 60. The silica gel layer was additionally washed with 30 mL of dichloromethane. The combined organic elute was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ether, 20:1, vol.) to give 0.62 g (30%) of yellowish solid.

Provenance & Evidence