2-Propenoic acid, 3-phenyl-, methyl ester → Methyl 4-phenyl-1H-pyrrole-3-carboxylate

HRID 554226Notes

Reaction equation

HRID 554226 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[C:14]([O:24][CH3:25])(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[K+]>>[C:17]1([C:16]2[C:15]([C:14]([O:24][CH3:25])=[O:23])=[CH:10][NH:11][CH:12]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylateYield 52.2%

Procedure

Using p-toluenesulfonylmethyl isocyanide (10.1 g), methyl cinnamate (8.33 g) and potassium tert-butoxide (6.97 g), a procedure as in Reference Example 39 was performed to give the title compound as pale-yellow crystals (yield 5.40 g, 52%).

Sources & evidence

ORD record
ord-438611cc20004520a93edf229b991950
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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