1,1,3,3-Tetramethylguanidine → HCID 69563048, compound

HRID 2181185Notes

Reaction equation

HRID 2181185 reaction equation
CC1C2C(=CC=C(C=O)C=2)NC=1.[Cl-].C(OC([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C(OCC)=O)C.CN(C)C(=N)N(C)C.[CH2:50]([O:52][C:53](=[O:69])/[C:54](/[O:66][CH2:67][CH3:68])=[CH:55]/[C:56]1[CH:57]=[C:58]2[C:62](=[CH:63][CH:64]=1)[NH:61][CH:60]=[C:59]2[CH3:65])[CH3:51]>ClCCl>[CH2:50]([O:52][C:53](=[O:69])[CH:54]([O:66][CH2:67][CH3:68])[CH2:55][C:56]1[CH:57]=[C:58]2[C:62](=[CH:63][CH:64]=1)[NH:61][CH:60]=[C:59]2[CH3:65])[CH3:51]

Participants

6

Reactant 4

HCID 664601,1,3,3-TetramethylguanidineHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)HCID 22485678HCID 22485678, compoundHCID 69563611HCID 69563611, compound

Product 1

HCID 69563048HCID 69563048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedures described in preparation 1a) and 1b), 3-methyl-1H-indole-5-carbaldehyde [Helv. Chim. Acta (1968), 51(7), 1616-28] 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-(3-methyl-1H-indol-5-yl)-acrylic acid ethyl ester, which was subsequently hydrogenated to yield the title compound as colorless oil.

Workup

  1. customto give

Sources & evidence

ORD record
ord-4211262c41624143b722d76f3d459428
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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