1,1,3,3-Tetramethylguanidine → (Z)-2-ethoxy-3-(2-methyl-1H-indol-5-yl)-acrylic acid ethyl ester

HRID 2181187Notes

Reaction equation

HRID 2181187 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH:11]=O)=[CH:6][CH:5]=2.[Cl-].[CH2:14]([O:16][CH:17]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:15].CN(C)C(=N)N(C)C>ClCCl>[CH2:21]([O:20][C:18](=[O:19])/[C:17](/[O:16][CH2:14][CH3:15])=[CH:11]/[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([CH3:1])=[CH:10]2)[CH3:22]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)HCID 218655092-methyl-1H-indole-5-carbaldehyde

Product 1

HCID 69563061(Z)-2-ethoxy-3-(2-methyl-1H-indol-5-yl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedures described in preparation 1a) and 1b), 2-methyl-1H-indole-5-carbaldehyde was reacted with (1,2-diethoxy-2-oxoethyl)triphenyl phosphonium chloride in dichloromethane in the presence of tetramethyl guanidine to give (Z)-2-ethoxy-3-(2-methyl-1H-indol-5-yl)-acrylic acid ethyl ester, which was subsequently hydrogenated to yield the title compound as colorless oil.

Sources & evidence

ORD record
ord-e780d2826e474d5a8220a8e3170f6a61
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

Loading…