Sodium borohydride → 2-(3,4-Difluorophenyl)ethan-1-ol

HRID 2301244Notes

Reaction equation

HRID 2301244 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 226673252-(3,4-Difluorophenyl)acetaldehyde

Product 1

HCID 27583132-(3,4-Difluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1 liter three-necked flask equipped with a stirrer, 33.29 g (213 mmol) of (3,4-difluorophenyl) acetaldehyde and 426 ml of ethanol were charged, to which 8.85 g (234 mmol) of sodium borohydride were added, and the mixture was stirred overnight. Ethanol was distilled off, and 1N hydrochloric acid and ether were added. An organic layer and an aqueous layer were separated, the aqueous layer was extracted with ether, the extract combined with the organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, the solvent was distilled off and condensed, the concentrate was purified by vacuum distillation to obtain 17.59 g (52%, bp 110-121° C./16-22 Torr.) of the title compound as oily product.

Workup

  1. customInto a 1 liter three-necked flask equipped with a stirrer
  2. additionwere added
  3. distillationEthanol was distilled off
  4. addition1N hydrochloric acid and ether were added
  5. customAn organic layer and an aqueous layer were separated
  6. extractionthe aqueous layer was extracted with ether
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationThe desiccating agent was filtered off
  9. distillationthe solvent was distilled off
  10. customcondensed
  11. distillationthe concentrate was purified by vacuum distillation

Sources & evidence

ORD record
ord-e7704639a40d4789bee9f7b99cca1b53
Source dataset
uspto-grants-2002_12
Patent number
US06500503B2

Reaction notes

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