Lithium borohydride → 2-(3-Nitrophenyl)propan-1-ol
Reaction equation
[BH4-].[Li+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([CH3:17])[C:13](OC)=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C1COCC1>[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([CH3:17])[CH2:13][OH:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of lithium borohydride (2M, THF, 2.0 equiv. 3.4 ml) was added to a solution of methyl 2-(3-nitrophenyl)propanoate (0.7 g) in THF. The resulting mixture was stirred for 18 hours then concentrated and poured into hydrochloric acid (10%) at 0□C. The mixture was extracted with ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated to afford the title compound as yellow oil (0.610 g, 100% yield).
Workup
- concentrationthen concentrated
- additionpoured into hydrochloric acid (10%) at 0□C
- extractionThe mixture was extracted with ether
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3d4160e9542345fd9bf552d9af0c8a4d
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592346B2
Reaction notes
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