Water → 2-Chloro-4-(n-pentyl)benzyl alcohol

A solution (1.0 M, 2.4 ml) of tetrabutylammonium fluoride/tetrahydrofuran was added to a solution of 1-((tert-butyldiphenylsilyloxy)methyl)-2-chloro-4-(n-pentyl)benzene (890 mg) in tetrahydrofuran (4.5 ml) under ice-cooling, and the mixture was stirred for 2 hr. Water was added to the reaction mixture and the resulting product was extracted three times with ethyl acetate. The organic layers were combined and washed successively with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give the objective compound (345 mg) as a colorless oil.

1. temperaturecooling
2. extractionthe resulting product was extracted three times with ethyl acetate
3. washwashed successively with diluted hydrochloric acid
4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
5. customThe solvent was evaporated
6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

ORD record

ord-d4ae530da7514597bccb88800af7f1de

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06911469B2