4-Phenylbenzyl chloride → HCID 68825173, compound

HRID 1188014Notes

Reaction equation

HRID 1188014 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1.C(O[K])(C)(C)C.Cl[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>C1COCC1.CN(C=O)C>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([CH2:26][O:17][CH2:16][C:15]2[N:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:18])=[CH:5][CH:6]=3)[CH:12]=[N:13][CH:14]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 154634-Phenylbenzyl chlorideHCID 68822221HCID 68822221, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 68825173HCID 68825173, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(5-hydroxymethylimidazol-1-ylmethyl)benzoic acid methyl ester of Example A2 (0.11 g, 0.44 mmol) in THF (4 ml), DMF (1 ml) was added portionwise tBuOK (50 mg, 0.44 mmol). The reaction mixture was stirred at room temperature for 1.5 h, then 4-chloromethylbiphenyl (90 mg, 0.44 mmol) in THF (1 ml) 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 AcOEt. The organic phase was dried over MgSO4 and the resulting oil was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 95/05) to give a yellow solid (20 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 AcOEt
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe resulting oil was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 95/05)

Sources & evidence

ORD record
ord-9c8dcb09b8724ab581d2c496b7746358
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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