Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 19870610, compound

HRID 330160Notes

Reaction equation

HRID 330160 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=O)=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.[CH3:14][O:15][C:16](=[O:37])[CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8](/[CH:12]=[CH:17]/[C:16]([O:15][CH3:14])=[O:37])[CH:7]=2)[C:3](/[CH:1]=[CH:17]/[C:16]([O:15][CH3:14])=[O:37])=[CH:4]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 19870558HCID 19870558, compound

Product 1

HCID 19870610HCID 19870610, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3,6-diformylindole (1 g), methyl(triphenylphosphoranylidene)acetate (7.76 g) and dry dioxane (50 ml) was stirred and heated under reflux for 6 hr under an atmosphere of nitrogen. The solvent was evaporated, the residue extracted with several portions of ether, the ether extracts evaporated and the crude product purified by flash chromatography, eluting with 2:3 ethyl acetate:hexane, to give dimethyl E,E-indole-3,6-diacrylate (1.2 g, 73%) as a yellow solid; partial NMR (250 MHz, DMSO-d6): 3.71(s, 3H, OCH3), 3.73(s, 3H, OCH3), 6.40(d, J=16.0 Hz, 1H, olefinic H); 6.60(d, J=16.0 Hz, 1H, olefinic H); 12.02(br s, 1H, NH).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hr under an atmosphere of nitrogen
  3. customThe solvent was evaporated
  4. extractionthe residue extracted with several portions of ether
  5. customthe ether extracts evaporated
  6. customthe crude product purified by flash chromatography
  7. washeluting with 2:3 ethyl acetate

Sources & evidence

ORD record
ord-688bedbd11ca405aa4509a4852d05a50
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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