Sodium borohydride → HCID 178436178, compound

HRID 221118Notes

Reaction equation

HRID 221118 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[C:12]([O:17]CC3C=CC=CC=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=O)=[CH:5][CH:4]=1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:11]2[C:12]([OH:17])=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66607920HCID 66607920, compound

Product 1

HCID 178436178HCID 178436178, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above 2-benzyloxy-3-pyridyl 4-ethylphenyl ketone (1.69 g) was dissolved in ethanol (15 ml), and thereto was added sodium borohydride (403 mg), and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The mixture was washed with water and successively with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give crude 2-benzyloxy-3-pyridyl-4-ethylphenylmethanol as colorless oil, which was used in the subsequent step without further purification. (3) The above 2-benzyloxy-3-pyridyl-4-ethylphenylmethanol was dissolved in methanol (10 ml), and thereto were added concentrated hydrochloric acid (1.0 ml) and 10% palladium-carbon (500 mg). The mixture was stirred at room temperature for 15 hours under hydrogen atmosphere under normal pressure. Insoluble materials were filtered off, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water and successively with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0-97:3) to give the desired 3-(4-ethylphenylmethyl)-2-hydroxypyridine (307 mg) as a pale brown solid. APCI-Mass m/Z 214 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe mixture was washed with water and successively with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give crude 2-benzyloxy-3-pyridyl-4-ethylphenylmethanol as colorless oil, which
  7. customwas used in the subsequent step without further purification
  8. dissolution(3) The above 2-benzyloxy-3-pyridyl-4-ethylphenylmethanol was dissolved in methanol (10 ml)
  9. additionwere added concentrated hydrochloric acid (1.0 ml) and 10% palladium-carbon (500 mg)
  10. stirringThe mixture was stirred at room temperature for 15 hours under hydrogen atmosphere under normal pressure
  11. filtrationInsoluble materials were filtered off
  12. customthe solvent was evaporated under reduced pressure
  13. dissolutionThe residue was dissolved in ethyl acetate
  14. washthe solution was washed with water and successively with brine
  15. dry with materialdried over sodium sulfate
  16. customThe solvent was evaporated under reduced pressure
  17. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:0-97:3)

Sources & evidence

ORD record
ord-9b35107bcdd94a17ab3f84fe2ef7ea73
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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