Hydrochloric Acid → (2-Pyrid-3-ylphenyl)methanol

HRID 1512271Notes

Reaction equation

HRID 1512271 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[O:10])[CH:2]=1.[BH4-].[Na+].Cl>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][OH:10])[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 38575932-(Pyridin-3-Yl)BenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 7537538(2-Pyrid-3-ylphenyl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-pyridin-3-yl-benzaldehyde (1 g, 5.46 mmole) in methanol (10 ml) was added a solution of NaBH4 (0.26 g, 6.82 mmole) in methanol (10 ml) at 0° C. and stirred for 30 min at same temperature and then refluxed for 1 h. The unreacted NaBH4 was decomposed by solution of 6N HCl. The solvent was removed under reduced pressure and the residue was dissolved in 5N NaOH (20 ml) and extracted with ethyl acetate (3×20 ml). Combined organic extracts were dried (Na2SO4), filtered and concentrated to yield 0.95 g (94%) of product. MS (ESI+) m/z 186 (M+H)+.

Workup

  1. temperaturerefluxed for 1 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 5N NaOH (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialCombined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9cceab8b4bc649c79308abd304136ef2
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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