Water → 5-Trifluoromethyl-indan-2-yl-methanol
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12](O)=[O:13])[CH2:6]2.B.O>C1COCC1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][OH:13])[CH2:6]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The above 5-trifluoromethyl-indan-2-carboxylic acid (1.03 g, 4.47 mmol) was dissolved in THF (25 mL) and cooled to 0° C. To this solution was added a solution of borane in THF (1M, 6.5 mL). The mixture was warmed to room temperature and stirred for 1 hr. The mixture was treated with water (5 mL) and solvents were evaporated. The residue was extracted with ether and hydrochloric acid (1M). The organic phase was washed with brine and sodium bicarbonate solution. The ether solution was dried and solvents were evaporated to give oily material as 5-trifluoromethyl-indan-2-yl-methanol (0.98 g).
Workup
- temperatureThe mixture was warmed to room temperature
- customwere evaporated
- extractionThe residue was extracted with ether and hydrochloric acid (1M)
- washThe organic phase was washed with brine and sodium bicarbonate solution
- dry with materialThe ether solution was dried
- customsolvents were evaporated
Sources & evidence
- ORD record
- ord-fdad3ff1ca1b4aeab707bd15f25a1d48
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652053B2
Reaction notes
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