Pentane → HCID 12973062, compound

Temperature

-5 °C

A solution of benzo[b]furan (1.50 g, 12.7 mmol) in dry THF (50 ml) was cooled to −8° C. under a stream of argon. Tert-butyllithium (15.2 mmol, 10.2 ml of a 1.5 molar pentane solution) was added dropwise in such a way that a reaction temperature of −5° C. was not exceeded. Once all the substance had been added, the reaction mixture was stirred for 2½ hours at −5° C. A solution of 4-dimethylamino-4-phenylcyclohexanone (2.76 g, 12.7 mmol) in dry THF (15 ml) was added dropwise at 0° C. The mixture was stirred for 1 hour at 0° C. and then 4 days at ambient temperature. The reaction mixture was quenched with saturated ammonium chloride solution (30 ml), the organic phase was separated and the aqueous phase extracted four times with dichloromethane (30 ml). The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under vacuum. Purification was carried out by flash chromatography with cyclohexane/ethylacetate (V:V=7:3) over silica gel. 1.02 g 1-benzofuran-2-yl-4-dimethylamino-4-phenylcyclohexanol with a melting point of 134–137° C. were obtained.

1. additionOnce all the substance had been added
2. stirringThe mixture was stirred for 1 hour at 0° C.
3. custom4 days
4. customat ambient temperature
5. customThe reaction mixture was quenched with saturated ammonium chloride solution (30 ml)
6. customthe organic phase was separated
7. extractionthe aqueous phase extracted four times with dichloromethane (30 ml)
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. filtrationfiltered
10. customthe solvent removed under vacuum
11. customPurification

ORD record

ord-9bd3c6a9057f43a7824b35e07c750bc3

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183436B2