Tosylmethyl isocyanide → Ethyl 4-methyl-1h-pyrrole-3-carboxylate

HRID 554186

Reaction equation

HRID 554186 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[C:14]([O:19][CH2:20][CH3:21])(=[O:18])/[CH:15]=[CH:16]/[CH3:17].CC(C)([O-])C.[K+]>>[CH3:17][C:16]1[C:15]([C:14]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][NH:11][CH:12]=1

Participants

4

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 429065Ethyl trans-crotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylateYield 71.1%

Procedure

Using p-toluenesulfonylmethyl isocyanide (8.55 g), ethyl crotonate (5.0 g) and potassium tert-butoxide (5.90 g), a procedure as in Reference Example 39 was performed to give the title compound as a pale-yellow solid (yield 4.77 g, 71%).

Sources & evidence

ORD record
ord-c31a5c841b6e47ee8805ad48720a6c35
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Linked notes

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