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

HRID 1849964Notes

Reaction equation

HRID 1849964 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 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanone (2.38 g, 10 mmol) in methanol (20 ml) at 0° C. is added sodium borohydride (379 mg, 10.5 mmol) in one portion. The resultant solution is allowed to warm to room temperature, and is then stirred at room temperature for 3 hours. The reaction is quenched with saturated aqueous ammonium chloride solution (200 ml) and extracted with chloroform (200 ml). The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuuo to give desired product as a brown solid (2.32 g)

Workup

  1. customThe reaction is quenched with saturated aqueous ammonium chloride solution (200 ml)
  2. extractionextracted with chloroform (200 ml)
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-0ba5604d72534a50bf49f6905b656d5f
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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