Sodium borohydride → (4-Cyclopentyl-3-(trifluoromethyl)phenyl)methanol

HRID 62795Notes

Reaction equation

HRID 62795 reaction equation
[CH:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=2[C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=2[C:14]([F:15])([F:16])[F:17])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866538674-Cyclopentyl-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 58020942(4-Cyclopentyl-3-(trifluoromethyl)phenyl)methanolYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyclopentyl-3-(trifluoromethyl)benzaldehyde (0.25 g, 1.032 mmol) in ethanol (2.5 mL) was added sodium borohydride (0.047 g, 1.238 mmol) and the mixture was stirred at room temperature for 2 h. The mixture was quenched with water, acidified with 6 N HCl, diluted with more water and extracted with CH2Cl2. The CH2Cl2 layer was washed with water, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (0.22 g). LCMS m/z=227.5 [M−H2O+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.72 (m, 4H), 1.77-1.89 (m, 2H), 1.93-2.05 (m, 2H), 3.19-3.28 (m, 1H), 4.52 (d, J=6 Hz, 2H), 5.28 (t, J=5.6 Hz, 1H), 7.52-7.6 (m, 3H).

Workup

  1. customThe mixture was quenched with water
  2. additiondiluted with more water
  3. extractionextracted with CH2Cl2
  4. washThe CH2Cl2 layer was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4f89604234a4d708fad3442fdb2380d
Source dataset
uspto-grants-2016_09
Patent number
US09447041B2

Reaction notes

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