Hydrochloric Acid → 4-Dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehyde

A 60% dispersion of sodium hydride in mineral oil (254 mg, 6.36 mmol) was added to a suspension of methoxymethyltriphenylphosphonium chloride (2.18 g, 6.36 mmol) in anhydrous tetrahydrofuran (5 ml) and anhydrous N,N-dimethylformamide (5 ml) under argon. The mixture was stirred at room temperature for 2 h. A solution of 4-dimethylamino-4-(3-fluorophenyl)cyclohexanone (1.0 g, 4.24 mmol) in anhydrous tetrahydrofuran (5 ml) and anhydrous N,N-dimethylformamide (5 ml) was then added dropwise in the course of 30 min and the mixture was stirred at room temperature overnight. 2 M hydrochloric acid (25 ml) was then added dropwise, while cooling with ice, and the mixture was stirred at room temperature for 5 h. Thereafter, the mixture was extracted with ethyl acetate (5×20 ml) and diethyl ether (3×20 ml). The aqueous phase was adjusted to pH 11 with 4 M sodium hydroxide solution and extracted with ethyl acetate (4×20 ml). The combined organic extracts from the alkaline solution were dried with sodium sulfate and concentrated i. vac.

1. stirringthe mixture was stirred at room temperature overnight
2. temperaturewhile cooling with ice
3. stirringthe mixture was stirred at room temperature for 5 h
4. extractionThereafter, the mixture was extracted with ethyl acetate (5×20 ml) and diethyl ether (3×20 ml)
5. extractionextracted with ethyl acetate (4×20 ml)
6. dry with materialThe combined organic extracts from the alkaline solution were dried with sodium sulfate
7. concentrationconcentrated i

ORDレコード

ord-1f0495ec445b434088db7cabc70807a6

出典データセット

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08288406B2