Methyl propiolate → 4-(1-Phenylamino-ethylidene)-pent-2-enedioic acid 5-ethyl ester 1-methyl ester

HRID 1410874Notes

Reaction equation

HRID 1410874 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7])[CH3:2].[CH3:16][O:17][C:18](=[O:21])[C:19]#[CH:20]>CO>[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH:20][C:5](=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 94928Ethyl 3-anilinobut-2-enoate

Product 1

HCID 867141384-(1-Phenylamino-ethylidene)-pent-2-enedioic acid 5-ethyl ester 1-methyl esterYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-phenylamino-but-2-enoic acid ethyl ester (7 g, 34.1 mmol) and propynoic acid methyl ester (4.6 mL, 51.2 mmol) in MeOH (114 mL) was refluxed for 48 h. The solvent was evaporated, and the crude oil was purified by silica gel chromatography (0-20% EtOAc/hexanes) to give 5.88 g of the title compound as an orange oil. MS: (+) m/z 290.27 (M+1).

Workup

  1. temperaturewas refluxed for 48 h
  2. customThe solvent was evaporated
  3. customthe crude oil was purified by silica gel chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1098176ed0904e769268c81f187e3a23
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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