Methanol → (1-Propylcyclobutyl)methanol

LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (dichloromethane) gave 1-3 (1.229 g, 87%).

1. extractionThe mixture was then extracted with dichloromethane (3×40 mL)
2. washthe combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each)
3. dry with materialThe organic solution was then dried (Na2SO4)
4. filtrationfiltered
5. customevaporated
6. customPurification by flash chromatography on silica gel (dichloromethane)

ORD record

ord-081cc9df8950478ca48b57a906302cc0

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091231B2