Sodium hydride → 1-Benzyl-3-(2-methoxycarbonylvinyl)pyrrole

HRID 11235

Reaction equation

HRID 11235 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)OCC)C.[CH2:16]([N:23]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:23]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:11][C:12]([O:14][CH3:15])=[O:13])=[CH:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 156784801-Benzyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 691390211-Benzyl-3-(2-methoxycarbonylvinyl)pyrroleYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% in mineral oil, 311 mg, 7.8 mmol) in DMF (15 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (1.64 g, 7.8 mmol) in DMF (3 ml). The mixture was stirred for 30 minutes at room temperature and cooled again. To the mixture was added dropwise a solution of 1-benzyl-3-formylpyrrole (1.2 g, 6.5 mmol) in DMF (2 ml). The reaction mixture was stirred for 12 hours at room temperature and poured into ice-water, and extracted with ethylacetate. The extract was washed with water and dried. The solvent was evaporated. The obtained white crystal was washed with i-Pr2O to give 1-benzyl-3-(2-methoxycarbonylvinyl)pyrrole (1.3 g). Yield: 83%.

Workup

  1. temperaturecooled again
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. washThe obtained white crystal was washed with i-Pr2O

Sources & evidence

ORD record
ord-f8ffdd4a3dcd491a8cc70900384a71ec
Source dataset
uspto-grants-2006_08
Patent number
US07098201B2

Linked notes

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