Sodium borohydride → 1-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol

HRID 41668Notes

Reaction equation

HRID 41668 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70622881-[2-(4-Chlorophenyl)-1,3-thiazol-5-yl]-1-ethanone

Product 1

HCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanolYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanone (5 g, 21 mmol) in methanol (100 ml) is added sodium borohydride (832 mg, 22 mmol) at room temperature. The reaction mixture is stirred at room temperature for 0.5 hour. The reaction mixture is quenched with 100 ml of an aqueous saturated solution of ammonium chloride, extracted with dichloromethane (2×150 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated to dryness to give 1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanol (4.88 g).

Workup

  1. customThe reaction mixture is quenched with 100 ml of an aqueous saturated solution of ammonium chloride
  2. extractionextracted with dichloromethane (2×150 ml)
  3. dry with materialThe combined organic extracts are dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9c642914da4d4470aa47031ae72f88b8
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

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