Benzyl Bromide → 4-(4-Benzyloxymethylimidazol-1-ylmethyl)benzoic acid

HRID 1188015Notes

Reaction equation

HRID 1188015 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[N:13]=[CH:12]2)=[CH:6][CH:5]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CN(C=O)C>[CH2:21]([O:17][CH2:16][C:14]1[N:13]=[CH:12][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:18])=[CH:5][CH:6]=2)[CH:15]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 121126144-(4-Hydroxymethylimidazol-1-ylmethyl)benzoic acid methyl ester

Product 1

HCID 688222454-(4-Benzyloxymethylimidazol-1-ylmethyl)benzoic acidYield 3.3%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 4-(4-hydroxymethylimidazol-1-yl-methyl)benzoic acid methyl ester of Example A1 (0.4 g, 1.6 mmol) in THF/DMF (6/4) was added portionwise NaH 60% (162 mg, 4 mmol). The reaction mixture was stirred at room temperature for 1.5 h, then benzyl bromide (328 mg, 1.92 mmol) was added and the reaction was stirred overnight. The solvent was removed under reduced pressure, then water (10 ml) was added and the mixture was extracted with CH2Cl2. The aqueous phase was acidified with HCl 1 N to pH=4 and extracted with CH2Cl2. The latest organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 95/05) to give a white solid (17 mg).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was removed under reduced pressure
  3. additionwater (10 ml) was added
  4. extractionthe mixture was extracted with CH2Cl2
  5. extractionextracted with CH2Cl2
  6. dry with materialThe latest organic phase was dried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 95/05)

Sources & evidence

ORD record
ord-6901f970f1af4877be32d31d0cd84a89
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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