Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-acrylic acid ethyl ester

HRID 1827682Notes

Reaction equation

HRID 1827682 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[CH:18]=[CH:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:10]=2[N:1]=1)[CH3:17]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

Product 1

HCID 693701253-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbaldehyde (4-7, 2 g, 12.34 mmol) and (carbethoxymethylene)triphenylphosphorane (4.3 g, 12.34 mmol) in toluene (60 mL) was heated to reflux for 4 hours and stirred at ambient temperature for 12 hours. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 50% EtOAc/hexanes) to give 4-8 as a yellow solid.

Workup

  1. temperatureto reflux for 4 hours
  2. customremoval of the solvent
  3. customthe residue was chromatographed (silica gel, 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d88f201547e043bd9c108d4312166085
Source dataset
uspto-grants-2006_06
Patent number
US07056909B2

Reaction notes

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