1,2-dimethyl-1H-imidazole-5-carbaldehyde → (1,2-dimethyl-1H-imidazol-5-yl)methanol

HRID 630098

Reaction equation

HRID 630098 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]1[CH3:11]>CO>[CH3:3][N:4]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]1[CH3:11]

Participants

4

Reactant 2

HCID 31596101,2-dimethyl-1H-imidazole-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 304328(1,2-dimethyl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (457 mg, 12.1 mmol) in methanol (25 mL) was added a solution of 1,2-dimethyl-1H-imidazole-5-carbaldehyde (1.0 g, 8.1 mmol) in methanol (10 mL) at 0° C. The mixture was stirred overnight at room temperature. The solvent was evaporated, and crude (1,2-dimethyl-1H-imidazol-5-yl)methanol was obtained and used in the next step without purification; 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 3.45 (s, 3H), 4.34 (s, 2H), 5.05 (bs, 1H), 6.57 (s, 1H).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cc2a856618074041b0630d2806457f6b
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Linked notes

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