Triethylamine → HCID 131728143, compound

Participants

Reaction Steps

A yellow solution of 16, Et3N, ethyl acrylate and dichlorobis(triphenylphosphine) palladium(II) in DMF (25 mL, anhydrous, Aldrich) was stirred overnight under N2 at 110° C. After 16 h the reaction was allowed to cool to RT, filtered, and the filtrate diluted with ether (100 mL) and water (100 mL). The ether layer was rinsed with water (2×75 mL) and brine (1×74 mL) then dried (MgSO4) and concentrated to 5.75 g of a yellow solid. The crude product was purified first by column chromatography on 250 g silica gel with 2% EtOAc/hexanes to yield 6.22 g of an impure white solid. Crystallization from hexanes (˜100 mL) afforded 2.39 g (55%) of the title compound 17 as a crystalline white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.63 (d, J=8.0 Hz, 2H), 7.59 (d, J=16.1 Hz, 1H), 7.15-7.30 (m, 7H), 6.56 (d, J=16.1 Hz, 1H), 4.15 (q, J=7.1 Hz, 2H), 1.91 (s, 2H), 1.88 (s, 2H), 1.21-1.25 (m, 5H), 0.88 (s, 6H), 0.87 (s, 6H).

Provenance & Evidence