Water → trans-3-Octen-1-ol

LiAlH4 (13.5 mL, 13.5 mmol, 1 M/THF) was added to an ice cold solution of (E)-oct-3-enoic acid (7-1, 1.86 g, 13.1 mmol) in THF (48 mL). The reaction was allowed to warm to room temperature and after 2 h, was cooled in an ice bath and 50 mL H2O was added slowly. NaOH (3 M, 50 mL) and H2O (50 mL) were added and the resulting mixture was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL) and was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (1.283 g, 76%).

1. temperaturewas cooled in an ice bath
2. extractionthe resulting mixture was extracted with dichloromethane (3×100 mL)
3. washThe combined organic layer was washed with brine (100 mL)
4. dry with materialwas then dried (Na2SO4)
5. filtrationfiltered
6. customevaporated
7. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

ORD-Eintrag

ord-85b4bd52aa6848f5bf8fa8c7e9ecf861

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09006464B2