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

HRID 554223Notes

Reaction equation

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

Participants

Reactant 3

HCID 161915Tosylmethyl isocyanide

HCID 519179Methyl pent-2-enoate

HCID 23665647Potassium tert-butoxide

Product 1

HCID 53419689Methyl 4-ethyl-1H-pyrrole-3-carboxylateYield 64%

Procedure

Using p-toluenesulfonylmethyl isocyanide (10.1 g), methyl 2-pentenoate (6.01 g) and potassium tert-butoxide (7.01 g), a procedure as in Reference Example 39 was performed to give the title compound as pale-yellow crystals (yield 5.05 g, 64%).

Sources & evidence

ORD record: ord-172882b642284e0bba6bb7c1b956104f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

Loading…