Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 67176177, compound

HRID 1188282Notes

Reaction equation

[CH:1]([C:3]1[N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1)=O.[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>C1(C)C=CC=CC=1>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH:1]=[CH:22][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:9]([CH3:16])[CH:10]=1)#[N:13]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile (15 g, 71.4 mmol) and (carbethoxymethylene)-triphenylphosphorane (27.5 g, 78.6 mmol) in toluene was heated to 100° C. overnight. Then it was cooled to room temperature, concentrated and purified by silica gel column chromatography (PE:EA=5:1) to afford ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)acrylate as a yellow oil (19.8 g, 98%).

Workup

temperatureThen it was cooled to room temperature
concentrationconcentrated
custompurified by silica gel column chromatography (PE:EA=5:1)

Sources & evidence

ORD record: ord-309f80754b684fb3a7e6555f6433d3b3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673961B2

Reaction notes

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