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

HRID 1167975Notes

Reaction equation

HRID 1167975 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][CH:25]=[C:24]1[CH:28]=O)[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][CH:25]=[C:24]1[CH:28]=[CH:11][C:12]([O:14][CH3:15])=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 111269641-benzyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 691390871-Benzyl-2-(2-methoxycarbonylvinyl)pyrroleYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% in mineral oil, 960 mg, 24 mmol) in DMF (20 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (5.04 g, 24 mmol) in DMF (1 ml). The mixture was stirred for 15 minutes at room temperature and cooled again. To the mixture was added dropwise a solution of 1-benzyl-2-formylpyrrole (3.7 g, 20 mmol) in DMF (2 ml). The reaction mixture was stirred for 4 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 isopropylether to give 1-benzyl-2-(2-methoxycarbonylvinyl)pyrrole (3.14 g). Yield: 65%.

Workup

  1. temperaturecooled again
  2. stirringThe reaction mixture was stirred for 4 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 isopropylether

Sources & evidence

ORD record
ord-91ddb200317c4479867d845517bab047
Source dataset
uspto-grants-2003_09
Patent number
US06620841B1

Reaction notes

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