Sodium borohydride → HCID 17981653, compound

HRID 2252044Notes

Reaction equation

HRID 2252044 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH:19]=[O:20])=[CH:5][CH:4]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH2:19][OH:20])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 179818001-[(4-Methoxyphenyl)methyl]-4-phenyl-1H-imidazole-2-carbaldehyde

Product 1

HCID 17981653HCID 17981653, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Treat a solution of 1-(4-methoxybenzyl)-2-formyl-4-phenylimidazole (1.75 g, 5.99 mmol) in CH2Cl2/MeOH (1:1, 60 mL) with NaBH4 (480 mg, 12.7 mmol) at room temperature for 15 minutes. Quench with H2O (50 mL), extract with CH2Cl2 (2×100 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, CH2Cl2/MeOH 20:1→7:1) to provide 1.69 g (96% yield). MS(ES+): m/z=295 (M+H)+

Workup

  1. customQuench with H2O (50 mL)
  2. extractionextract with CH2Cl2 (2×100 mL)
  3. dry with materialdry (Na2SO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography (SiO2, CH2Cl2/MeOH 20:1→7:1)
  6. customto provide 1.69 g (96% yield)

Sources & evidence

ORD record
ord-3228954a65ad432e81e83403d2767f96
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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