반응식
[H-].[Na+].[CH:3]1([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](OCC)=[O:20]>>[CH3:13][O:12][C:10](=[O:11])[CH:9]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[C:19]([C:15]1[O:14][CH:18]=[CH:17][CH:16]=1)=[O:20]참가 물질
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- 온도
- 0 °C
실험 절차
To an ice cold suspension of 0.92 g (23 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) (previously washed with hexane and dried under vacuum) in 25 mL of 1,2-dimethoxyethane (DME) was added 0.9 g (5.76 mmol) of methyl cyclohexylacetate, and the resulting mixture was stirred at 0° C. for 20 min. Then 1.2 g (8.56 mmol) of ethyl 2-furoate was added, and the reaction mixture was heated at reflux overnight. The mixture was then cooled to 0° C., quenched by the addition of 1 M HCl solution to pH=3, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give a brown oil which was chromatographed on silica gel (Biotage; 10% hexane in dichloromethane) to afford 1.1 g (76% yield) of desired 2-cyclohexyl-3-furan-2-yl-3-oxo-propionic acid methyl ester as indicated by 1H NMR.
후처리
- washpreviously washed with hexane
- dry with materialdried under vacuum) in 25 mL of 1,2-dimethoxyethane (DME)
- temperaturethe reaction mixture was heated
- temperatureat reflux overnight
- temperatureThe mixture was then cooled to 0° C.
- customquenched by the addition of 1 M HCl solution to pH=3
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto give a brown oil which
- customwas chromatographed on silica gel (Biotage; 10% hexane in dichloromethane)
출처 및 근거
- ORD 기록
- ord-43ccc260727e4fae9c64489066b82bed
- 출처 데이터셋
- uspto-grants-2008_11
- 특허 번호
- US07449488B2
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