Boron trifluoride etherate → HCID 86032840, compound

Participants

Reaction Steps

Boron trifluoride etherate (0.65 mL) was added in one portion to a stirred solution of [4-(isopentyloxy)phenyl]acetic acid (crude from preparation of intermediate 11; 7.31 g, 32.9 mmol) and t-butyltrichloroacetimidate (14.4 g, 11.8 mL, 65.8 mmol) in THF (70 mL) at room temperature under nitrogen. The resulting solution was stirred for 16 h then quenched with saturated aqueous sodium hydrogen carbonate solution (50 mL). The resulting suspension was extracted with ethyl acetate (3×50 mL) then the organic_extracts combined, dried_(magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (5-10% diethyl ether: cyclohexane) to give the title compound as a colourless oil (3.82 g, 42% over 2 steps). LC/MS: 3.94 min; z/e 296, calcd (M+18) 296. 1H NMR (400 MHz: CDCl3): 7.25 (2H), 6.90 (2H), 4.05 (2H), 3.55 (2H), 1.90 (1H), 1.75 (2H), 1.50 (9H), 1.05 (6H).

Provenance & Evidence