Acetic Acid → alpha-Cyclopropyl-4-fluorobenzenemethanol

HRID 65231Notes

Reaction equation

HRID 65231 reaction equation
[CH:1]1([C:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=O)[CH2:3]C1.[BH4-].[Na+].C(O)(=[O:18])C>C(O)C>[CH:4]1([CH:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[OH:18])[CH2:1][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 201883591-Cyclopropyl-2-(4-fluorophenyl)ethanone

Product 1

HCID 102498alpha-Cyclopropyl-4-fluorobenzenemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 3.2 g (0.085 mole) cyclopropyl-4-fluorobenzylmethanone to 80 ml of 3.2 g (0.085 mole) sodium borohydride partially dissolved in absolute ethanol, following the reaction by thin-layer chromatography. After about 6 hours at room temperature, cool the reaction in an ice bath and add acetic acid. Extract the mixture with methylene (3×60 ml) wash the methylene chloride extracts with saturated aqueous sodium bicarbonate solution, and dry over magnesium sulfate. Evaporate the methylene chloride extracts and dry in vacuo to yield the title compound.

Workup

  1. customthe reaction by thin-layer chromatography
  2. temperaturecool
  3. customthe reaction in an ice bath
  4. extractionExtract the mixture with methylene (3×60 ml)
  5. washwash the methylene chloride
  6. dry with materialdry over magnesium sulfate
  7. customEvaporate the methylene chloride extracts
  8. customdry in vacuo

Sources & evidence

ORD record
ord-35a7627a22d040378fe6df06d6d72072
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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