2-Methylbenzylideneacetoacetic acid ethyl ester → 5-Methyl-7-(2-methylphenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid diethyl ester

HRID 1415313Notes

Reaction equation

HRID 1415313 reaction equation
C(O[C:4](=O)[CH2:5][C:6]([CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=O)C.[C:18]([CH:23]=[C:24]1[CH2:28]C[CH2:26][NH:25]1)([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH2:21]([O:20][C:18]([C:23]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:6]2[N:25]([CH2:26][CH2:4][CH2:5]2)[C:24]=1[CH3:28])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 540400732-Methylbenzylideneacetoacetic acid ethyl esterHCID 68118984Ethyl (pyrrolidin-2-ylidene)acetate

Product 1

HCID 123779435-Methyl-7-(2-methylphenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid diethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon boiling a solution of 7.7 g of 2-methylbenzylideneacetoacetic acid ethyl ester and 5.6 g of carbethoxymethylidenepyrrolidine in 50 ml of ethanol for 8 hours, 5-methyl-7-(2-methylphenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid diethyl ester of melting point 148° (alcohol) is obtained. Yield: 62% of theory.

Workup

  1. customfor 8 hours

Sources & evidence

ORD record
ord-51f263214c8143059703e20378693a77
Source dataset
uspto-grants-1977_01
Patent number
US04004015

Reaction notes

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