Ethyl benzoylformate → HCID 11020409, compound

Participants

Reaction Steps

The title compound was prepared according to a literature procedure (T. Akiyama, K. Ishikawa and S. Ozaki, Chemistry letters 1994, 627). To a solution of ethyl benzoylformate (2.5 g, 14.0 mmol) and allyl trimethylsilane (2.7 ml, 16.9 mmol) in 31 ml of methylene chloride (anhydrous) at −78° C. was added 1.6 ml of tin chloride (14.28 mmol) dropwise. The cooling bath was removed after the addition was complete. After the reaction mixture was stirred at room temperature for 5 min., TLC showed the reaction was complete. Triethylamine (3.5 ml) and water (150 ml) were added to quench the reaction. Extraction with ethyl acetate was complicated by the emulsion which was broken up by filtration through celite. The extracts were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography with methylene chloride/hexane=2.5:97.5 to afford 2-hydroxyl-2-phenyl-4-pentenoic acid, ethyl ester as an oil (1.2 g). 400 MHz 1H NMR (CDCl3): δ 7.59 (m, 2H); 7.29 (m, 3H); 5.79 (m, 1H); 5.13 (m, 2H); 4.23 (m, 2H); 2.96 (m, 1H); 2.74 (m, 1H); 1.26 (t, J=7.0 Hz, 3H).

Provenance & Evidence