Water → (2,6-Diisopropylphenyl)[1-(2'-methoxybiphenyl-3-yl)ethylidene]amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.78 g (7.75 mmol) of 13 in 30 mL of THF, 3.10 mL (7.75 mmol) of 2.5 M nBuLi in hexanes was added at −100° C. The reaction mixture was stirred for 1 hr at −70° C., then cooled to −100° C., and 8.35 mL (8.35 mmol) of 1M ZnCl2 in THF was added. The resulting mixture was slowly warmed to room temperature, stirred for 12 hr at this temperature, and then 1.45 g (7.75 mmol) of 2-bromoanisole and 85 mg (0.15 mmol) of Pd(PtBu3)2 were added. The resulting mixture was refluxed for 3 hr, and then 5 mL of water was added. This mixture was passed through short layer of silica gel 60 (40-63 um) which was then additionally washed with 30 mL of dichloromethane. The combined organic filtrate was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60(40-63 um, eluent: from hexanes to hexanes-diethyl ether=20:1, vol.). This procedure gave 2.36 g (79%) of the title product.

Provenance & Evidence