Diazomethane → methyl 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

HRID 638314Notes

Reaction equation

HRID 638314 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[N+](=[CH2:24])=[N-]>ClCCl>[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([O:19][CH3:24])=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 134870625-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid

Product 1

HCID 13487006methyl 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg of 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid in 5 ml of dichloromethane is treated with an excess of ethereal diazomethane, and the reaction mixture is maintained at room temperature for 30 minutes. The solvents and excess reagent are eliminated under reduced pressure and the residue crystallized from ethyl acetate-methanol, to yield methyl 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate. Likewise but using diazoethane, diazopropane and diazobutane in place of diazomethane there are respectively obtained:

Workup

  1. customthe residue crystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-73a5f67edfc748e69fa496fdfbe1af71
Source dataset
uspto-grants-1985_12
Patent number
US04560699

Reaction notes

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