Sodium borohydride → 5-hydroxymethyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
- extractionextracted with ethyl acetate
- dry with materialdried with Na2SO4
- customevaporated
- customto give the crude as an oil
- 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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