Sodium borohydride → 5-hydroxymethyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester

HRID 491578Notes

Reaction equation

HRID 491578 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]=[O:11])=[N:8][N:7]([CH3:12])[N:6]=1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH2:10][OH:11])=[N:8][N:7]([CH3:12])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86606414HCID 86606414, compound

Product 1

HCID 672153975-hydroxymethyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl esterYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.6 g (13.3 mmol) of 5-formyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester (see Example 2a) in methanol (100 ml) was treated with NaBH4 (601 mg) under stirring for 1 hour at ambient temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried with Na2SO4 and evaporated to give the crude as an oil. Purification on silica gel in ethyl acetate:hexane (2:1) yielded 1.85 g (81%) of the crystalline product, m.p. 112-113° C.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customto give the crude as an oil
  6. customPurification on silica gel in ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-5d5c8fe9494b430bb99e2df851c29f86
Source dataset
uspto-grants-2009_05
Patent number
US07531559B2

Reaction notes

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