Sodium borohydride → 1-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol

HRID 2309802

Reaction equation

HRID 2309802 reaction equation
[C:1]1([C:7]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:13]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH:7]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[N:13]=2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 140969581-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone

Product 1

HCID 140969591-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanolYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (675 mg, 0.0025 mol) in methanol (40 mL) was added sodium borohydride (300 mg, 0.0079 mol) in portions and the mixture allowed to stir at room temperature for one hour. The reaction mixture was concentrated, diluted with water, and extracted with ether (3×25 mL). The combined extracts were washed with brine, dried over magnesium sulfate, concentrated, and chromatographed. Recrystallization from hexane/ethyl acetate afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl)methanol (300 mg, 45%). mp. 146°-147° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ether (3×25 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed
  8. customRecrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-5d6a10867a7f4dada197feda6a8d533f
Source dataset
uspto-grants-1987_09
Patent number
US04697012

Linked notes

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