Ethyl Acetate → HCID 59464241, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triethylphosphonopropionate (12.5 g, 52.6 mmol) in THF (10 mL) was added in one portion to a stirred mixture of sodium hydride (60% in mineral oil, 2.3 g, 57.6 mmol) in THF (75 mL) and the reaction mixture was stirred at 11° C. under an argon atmosphere for 1 h. In a separate flask tetramethylguanidine (6.61 g, 57.4 mmol) was added in one portion to a solution of 4-(4-hydroxyphenyl)cyclohexanone (9.1 g, 47.8 mmol) in THF (40 mL) at 10° C. under an argon atmosphere and the stirred mixture was warmed to room temperature over 1 h. This mixture was added in one portion to the triethylphosphonopropionate mixture at 10° C. and the combined reaction mixture was warmed to ambient temperature and stirred for 18 h under an argon atmosphere. A saturated aqueous solution of ammonium chloride (75 mL) and EtOAc (100 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were dried and concentrated in vacuo to leave a residue. The residue was triturated with a mixture of ether and isohexane (2:1), filtered and the filtrate was concentrated in vacuo to give the title compound (6.9 g, 53%) as a solid; 1H NMR δ 1.21 (3H, t), 1.33-1.5 (2H, m), 1.78-2.1 (4H, m), 1.84 (3H, s), 2.6-2.78 (2H, m), 2.99-3.09 (1H, m), 4.12 (2H, q), 6.67 (2H, d), 7.02 92H, d), 9.08 (1H, s); MS m/e MH+ 275.

Provenance & Evidence