Methyl propiolate → HCID 86714138, compound

HRID 919868

Reaction equation

HRID 919868 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 86714138HCID 86714138, compoundYield 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-ab242cb9833242d9af20b9f7b5f7cb71
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Linked notes

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