Water → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol
Reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)C.[H-].C([Al+]CC(C)C)C(C)C.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:14][C:13]([F:15])([F:16])[C:10]1[CH:9]=[CH:8][C:7](/[CH:6]=[CH:5]/[CH2:4][OH:3])=[CH:12][CH:11]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the ester obtained in step 1 (37.1 g) in toluene (310 ml) at 0° C. was added dropwise diisobutylaluminum hydride (1.2M in toluene, 317 ml) and the solution was stirred at 0° C. for 1 h. Water (47.6 ml) was carefully added at 0° C. followed by sodium hydroxide 2M (47.6 ml) and finally water (95.1 ml). The mixture was allowed to stir at room temperature for 1 h. After filtration, the solution was washed with hydrochloric acid 2N, water and brine, dried over sodium sulfate and concentrated in vacuo to give 29.5 g of the desired alcohol as a solid (96%) which was characterized by its mass and NMR spectra.
Workup
- stirringto stir at room temperature for 1 h
- filtrationAfter filtration
- washthe solution was washed with hydrochloric acid 2N, water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2b324ce0b27144edb8ed68c8d30ceffc
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174987B2
Reaction notes
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