1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 3-formyl-4,5-dimethyl-1-vinylpyrrole-2-carboxylate

HRID 1107818Notes

Reaction equation

HRID 1107818 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([CH:11]=[O:12])=[C:5]1[C:13]([O:15][CH3:16])=[O:14].N12CCCN=C1CCCCC2>O1CCCC1>[CH:11]([C:6]1[C:7]([CH3:10])=[C:8]([CH3:9])[N:4]([CH:3]=[CH2:2])[C:5]=1[C:13]([O:15][CH3:16])=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18785723Methyl 1-(2-bromoethyl)-3-formyl-4,5-dimethylpyrrole-2-carboxylate

Product 1

HCID 18785679Methyl 3-formyl-4,5-dimethyl-1-vinylpyrrole-2-carboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.15 g (0.00052 mole) of methyl 1-(2-bromoethyl)-3-formyl-4,5-dimethylpyrrole-2-carboxylate and 0.08 g (0.00052 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene dissolved in 2 ml of tetrahydrofuran was heated under reflux for 6 hours. The reaction mixture was allowed to cool at room temperature and purified by column chromatography through silica gel using a 9:1 mixture of toluene and ethyl acetate as an eluent to give 0.080 g (74% yield) of methyl 3-formyl-4,5-dimethyl-1-vinylpyrrole-2-carboxylate as pale yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. custompurified by column chromatography through silica gel using
  4. additiona 9:1 mixture of toluene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-723399c805c649efb66aedc5f37b338d
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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