Water → HCID 66670221, compound

HRID 1514646Notes

Reaction equation

HRID 1514646 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[H-].[Na+].Cl[CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>O1CCCC1>[CH2:28]([O:27][CH2:26][N:3]1[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[C:2]1[CH3:1])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 66670204HCID 66670204, compound

Product 1

HCID 66670221HCID 66670221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 mg portion of benzyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 79 mg of sodium hydride (55% dispersion in oil) was added under ice-cooling, followed by stirring at room temperature for 30 minutes. A 0.357 ml portion of benzyl chloromethyl ether was added dropwise to this solution under ice-cooling, followed by stirring at room temperature for 1.5 hours. After adding water under ice-cooling, extraction was carried out with ethyl acetate. Then, after washing with saturated brine and then drying with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:8) to obtain 503 mg of benzyl 1-[(benzyloxy)methyl]-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate as a colorless liquid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 1.5 hours
  4. temperaturecooling
  5. extractionextraction
  6. washThen, after washing with saturated brine
  7. dry with materialdrying with anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:8)

Sources & evidence

ORD record
ord-f4d32a46369640008ded0a07c3496e09
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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