Phenyl-3-pyridinylmethanone → Phenyl(pyridin-3-yl)methanol

HRID 647086

Reaction equation

HRID 647086 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:8])[CH:10]=1

Participants

4

Reactant 2

HCID 21540Phenyl-3-pyridinylmethanoneHCID 4311764Sodium borohydride

Product 1

HCID 234839Phenyl(pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50.0 gms of phenyl-3-pyridyl ketone was added to 650 ml of methanol and the system was then cooled to 0° to 5° C. After cooling, 15.5 gms of sodium borohydride was added in 3 parts. After addition, the system was allowed to come to room temperature. The system was then refluxed for 1 hour and stirred for an additional 72 hours at room temperature. The methanol was removed by stripping. Afterwards, 575 ml of 5% HCl solution was added to the residue and the system refluxed for 15 minutes. The acid was neutralized with 50% NaOH solution and the product extracted with methylene chloride to give the 3-pyridylphenylcarbinol as a white solid, m.p. 53° to 60° C.

Workup

  1. temperaturethe system was then cooled to 0° to 5° C
  2. temperatureAfter cooling
  3. additionAfter addition
  4. customto come to room temperature
  5. temperatureThe system was then refluxed for 1 hour
  6. customThe methanol was removed by stripping
  7. additionAfterwards, 575 ml of 5% HCl solution was added to the residue
  8. temperaturethe system refluxed for 15 minutes
  9. extractionthe product extracted with methylene chloride

Sources & evidence

ORD record
ord-5ec55a0811504211a6dfdbfdd3ca43fb
Source dataset
uspto-grants-1983_10
Patent number
US04407806

Linked notes

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