Tosylmethyl isocyanide → Methyl 4-methyl-1H-pyrrole-3-carboxylate

HRID 554222Notes

Reaction equation

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

Participants

Reactant 3

HCID 161915Tosylmethyl isocyanide

HCID 638132Methyl Crotonate

HCID 23665647Potassium tert-butoxide

Product 1

HCID 15274278Methyl 4-methyl-1H-pyrrole-3-carboxylateYield 25%

Procedure

Using p-toluenesulfonylmethyl isocyanide (94.6 g), methyl crotonate (48.5 g) and potassium tert-butoxide (76.7 g), a procedure as in Reference Example 39 was performed to give the title compound as a pale-yellow solid (yield 16.8 g, 25%).

Sources & evidence

ORD record: ord-dc2a31e15c8942f6bb59000738d4cac4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

Loading…