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

HRID 1849974Notes

Reaction equation

HRID 1849974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]=[O: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]([CH2:13][OH:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 450368222-(4-Chlorophenyl)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 59562416[2-(4-Chlorophenyl)thiazol-5-yl]methanolYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-(4-chlorophenyl)thiazole-5-carbaldehyde (3.26 g, 14.6 mmol) in methanol (50 ml) is added the sodium borohydride (568 mg, 15 mmol) portionwise at room temperature. The reaction mixture is stirred at room temperature for 2 h. The reaction mixture is quenched with 50 ml of an aqueous saturated solution of ammonium chloride, extracted with dichloromethane (2×100 ml). The combined organic extracts are dried with magnesium sulphate, filtered and evaporated to dryness to give [2-(4-chlorophenyl)thiazol-5-yl]methanol (3.24 g).

Workup

  1. customThe reaction mixture is quenched with 50 ml of an aqueous saturated solution of ammonium chloride
  2. extractionextracted with dichloromethane (2×100 ml)
  3. dry with materialThe combined organic extracts are dried with magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-31e7fe97978645ac95802f4f75d84ec1
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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