Ethanol → HCID 21779761, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% dispersion in mineral oil, 535 mg, 13.4 mmol) in diethyl ether (25 mL) at 0° C. was added ethanol (0.06 ml, 1.03 mmol) dropwise. The grey suspension was stirred at 0° C. for 20 min. A solution of cycloheptanone (1.58 ml, 13.4 mmol) and ethyl formate (1.63 ml, 20.1 mmol) in diethyl ether (3 mL) was added dropwise over 10 min. The pale yellow heterogeneous reaction mixture was stirred at 0° C. for 1 h then warmed to room temperature for 4 h. The reaction was carefully quenched with ethanol (2 mL) then water (25 mL) was added. The layers were separated and the aqueous phase was washed with diethyl ether. The organic layers were set aside and later discarded. The aqueous layer was acidified with 1M HCl until pH=2 and then extracted with diethyl ether (2×). The combined organic layers were dried over MgSO4 and concentrated to afford 1.41 g (75%) of 2-[1-hydroxy-meth-(Z)-ylidene]-cycloheptanone as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ (ppm) 14.69 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 2.52-2.61 (m, 2H), 2.23-2.32 (m, 2H), 1.67-1.82 (m, 4H), 1.58-1.67 (m, 2H).

Provenance & Evidence