Ethanol → HCID 21779761, compound

Temperature

0 °C

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).

1. stirringThe pale yellow heterogeneous reaction mixture was stirred at 0° C. for 1 h
2. temperaturethen warmed to room temperature for 4 h
3. customThe reaction was carefully quenched with ethanol (2 mL)
4. additionwater (25 mL) was added
5. customThe layers were separated
6. washthe aqueous phase was washed with diethyl ether
7. extractionextracted with diethyl ether (2×)
8. dry with materialThe combined organic layers were dried over MgSO4
9. concentrationconcentrated

ORD record

ord-9d07df7ca036482080a232b5703378c1

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2