Benzoic Acid → [3-(Pyridin-3-yl)phenyl]methanol

HRID 1809164Notes

Reaction equation

HRID 1809164 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](O)=[O:11])[CH:2]=1.C(O)(=O)C1C=CC=CC=1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[CH2:10][OH:11])[CH:2]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 27955753-(Pyridin-3-yl)benzoic acid

Product 1

HCID 2795577[3-(Pyridin-3-yl)phenyl]methanolYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 100 mL recovery flask was added 3-(3-pyridyl)-benzoic acid 45 (2.00 g, 10.0 mmol, 1.0 eq.) and THF (20 mL). The resulting suspension is stirred. BH3 (1.0 M in THF, 15 mL, 15 mmol, 1.5 eq.) was added the resulting mixture was refluxed overnight. Incomplete reduction was observed by LC/MS. Additional BH3 (10 mL) was added and the mixture was refluxed for an additional 6 h. LC/MS indicates complete reduction of the benzoic acid. The reaction mixture was concentrated and diluted with EtOAc. The organic layer was washed with a succession of water, HCl, brine. The combined aqueous layers were extracted with EtOAc. The organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a clear oil. The crude material was purified via flash chromatography (40% to 60% EtOAc/Hex) to give a white solid (995 mg, 53%).

Workup

  1. temperaturewas refluxed overnight
  2. additionAdditional BH3 (10 mL) was added
  3. temperaturethe mixture was refluxed for an additional 6 h
  4. concentrationThe reaction mixture was concentrated
  5. additiondiluted with EtOAc
  6. washThe organic layer was washed with a succession of water, HCl, brine
  7. extractionThe combined aqueous layers were extracted with EtOAc
  8. dry with materialThe organic phases were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a clear oil
  12. customThe crude material was purified via flash chromatography (40% to 60% EtOAc/Hex)

Sources & evidence

ORD record
ord-d92f4bbcae2648ab977e26a87469f090
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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