Hydrochloric Acid → 3-(4-Chloro-2-(trifluoromethyl)-phenyl)propan-1-ol
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20](OC)=[O:21])=[C:14]([C:24]([F:27])([F:26])[F:25])[CH:13]=1.Cl>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[C:14]([C:24]([F:25])([F:26])[F:27])[CH:13]=1Participants
5
Conditions
- Temperature
- -78 °C
Procedure
Diisobutylaluminum hydride (20% in toluene, 34 ml) was added dropwise to a solution of methyl 3-(4-chloro-2-(trifluoromethyl)phenyl)propanoate (5 g) in DCM (150 ml) at −78° C. under nitrogen during 10 minutes. The mixture was then stirred at −78° C. for 1 hour before warming up to room temperature. The mixture was then carefully poured to crushed ice (500 g). After adding 5M HCl to pH 2, the mixture was extracted with DCM (200 ml×3), combined DCM layer was then dried over sodium sulphate, solvent was then removed under reduced pressure. The residue was clean enough for next step (4.5 g).
Workup
- temperaturebefore warming up to room temperature
- additionThe mixture was then carefully poured
- extractionthe mixture was extracted with DCM (200 ml×3)
- dry with materialwas then dried over sodium sulphate, solvent
- customwas then removed under reduced pressure
Sources & evidence
- ORD record
- ord-7a5a53bd5a334c81a2a03d32f55da922
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932251B2
Reaction notes
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