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

HRID 45907Notes

Reaction equation

HRID 45907 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-chlorophenyl)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 1 hour. The reaction mixture is quenched with saturated aqueous ammonium chloride solution (100 ml) and extracted with dichloromethane (2×150 ml). The combined organic extracts are dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to give 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol (4.88 g).

Workup

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

Sources & evidence

ORD record
ord-0fb724ba2dbf442d8e495a8f331d6d73
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

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