1-methyl-1H-1,3-benzodiazole-2-carbaldehyde → (1-methyl-1H-1,3-benzodiazol-2-yl)methanol

HRID 29456

Reaction equation

HRID 29456 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=[O:12].[BH4-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][OH:12]

Participants

5

Reactant 2

HCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 432 mg of 1-methyl-1H-benzoimidazole-2-carbaldehyde (2.7 mmol, 1 eq) dissolved in a mixture of THF (10 mL) and methanol (10 mL) was added 340 mg of sodium borohydride (9.0 mmol, 3.33 eq) in several portions. After 12 h the reaction mixture was quenched with water and extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (1-methyl-1H-benzoimidazol-2-yl)-methanol in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.8 (s, 3 H) 4.7 (d, J=5.6 Hz, 2 H) 5.6 (t, J=5.7 Hz, 1 H) 7.2 (m, 1 H) 7.2 (m, 1 H) 7.5 (m, 1 H) 7.6 (m, 1 H).

Workup

  1. customAfter 12 h the reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ad2e10d90d74c3faa56969db1eb728f
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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