Potassium Carbonate → (E)-3-(3'-Adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester

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A mixture of (E)-3-(3′-adamantan-1yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester (250 mg, 0.581 mmol) and K2CO3 (241 mg, 1.74 mmol) in water (2.9 ml) was stirred at RT for 30 min. Tetrabutylammonium hydrogen sulfate (197 mg, 0.581 mmol) and DCM (1.4 ml) were then added and the stirring maintained for further 10 min. A solution of carbonic acid iodomethyl ester propyl ester (184 mg, 0.755 mmol) in DCM (1.4 ml) was then added dropwise. The biphasic solution was stirred overnight at RT. After standard work-up and removal of the solvent under reduced pressure, the residue was taken up in Et2O. Tetrabutylammonium iodide was filtered off and the solvent was evaporated. (E)-3-(3′-Adamantan-1-yl-4′-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester was obtained (117 mg, 36%) after purification on silica gel (EtOAc/hexane 12:88).

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