Sodium borohydride → [1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-methanol

HRID 2169279Notes

Reaction equation

HRID 2169279 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:14]=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 218996431-(4-Trifluoromethyl-phenyl)-cyclopentanecarbaldehyde

Product 1

HCID 86725928[1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(4-trifluoromethyl-phenyl)-cyclopentanecarbaldehyde (238) (17.0 g, 70.24 mmol) in methanol (200 mL), was added NaBH4 (5.33 g, 140.5 mmol) portion-wise at 0° C. The reaction mixture was then stirred at room temperature for 2 h. After completion of the reaction, the solvent was concentrated and the crude product was diluted with water and extracted with ethyl acetate (2×300 mL). The organic part was dried over Na2SO4 and evaporated to give [1-(4-trifluoromethyl-phenyl)-cyclopentyl]-methanol (239) (15 g, 90%) as a white solid which was used for the next step without further purification.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe solvent was concentrated
  3. additionthe crude product was diluted with water
  4. extractionextracted with ethyl acetate (2×300 mL)
  5. dry with materialThe organic part was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-9767487757f647ca891327882c3caddc
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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