Benzenepropanoic acid, 4-fluoro-, ethyl ester → 3-(4-Fluorophenyl)propan-1-ol
Reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The product of Step b (20.0 g, 102 mmol) was dissolved in anhydrous THF (500 ml), and the mixture was cooled to 0° C. To this solution, 1M LAH in THF (100 ml) was added dropwise, then the mixture was allowed to come to room temperature and stirred for three days. The reaction was quenched by the careful sequential addition of water (3.8 ml), 15% NaOH (3.8 ml), and water (11.4 ml). The resulting slurry was stirred for 1 hour, the solids were removed by filtration and rinsed with EtOAc, and the combined filtrates were stripped to yield 15.4 g of a colorless oil. This material was used as-is in the next step. NMR (300 MHz, CDCl3) δ 7.20-7.05 (m, 2H); 6.97 (t, 2H, J=7 Hz); 3.69 (q, 2H, J=7 Hz); 2.70 (t, 2H, J=7 Hz); 1.88 (t of t, 2H, J=7, 7 Hz); 1.31 (t, 1H, J=7 Hz).
Workup
- customto come to room temperature
- customThe reaction was quenched by the careful sequential addition of water (3.8 ml), 15% NaOH (3.8 ml), and water (11.4 ml)
- stirringThe resulting slurry was stirred for 1 hour
- customthe solids were removed by filtration
- washrinsed with EtOAc
Sources & evidence
- ORD record
- ord-cefeac8203934e46ac4e33ff800247fe
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291744B2
Reaction notes
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