Ethanol → HCID 19813404, compound

HRID 467128Notes

Reaction equation

HRID 467128 reaction equation
[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[NH2:11]/[C:12](/[CH3:19])=[CH:13]\[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:20]([O:26][CH2:27][CH:28]=[CH2:29])(=[O:25])[CH2:21][C:22]([CH3:24])=O.[CH2:30](O)[CH3:31]>>[CH2:17]([O:16][C:14]([C:13]1[CH:22]([C:24]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:21]([C:20]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[C:30]([CH3:31])[NH:11][C:12]=1[CH3:19])=[O:15])[CH3:18]

Participants

5

Reactant 4

HCID 702EthanolHCID 70701Allyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 27716443-Ethynylbenzaldehyde

Product 1

HCID 19813404HCID 19813404, compound

Conditions

Temperature
80 °C

Procedure

In 20 ml of ethyl alcohol was dissolved 1.95 g (15 mmol) of 3-ethynylbenzaldehyde. Thereto were added 1.95 g (15 mmol) of ethyl 3-aminocrotonate and 2.1 g (15 mmol) of allyl acetoacetate, and the admixture was stirred with heating for 16 hours at 80° C. After completing the reaction, the reaction mixture was concentrated to give precipitate. After washing the obtained precipitate with ether, the precipitate was recrystallized from the mixture solution of n-pentane and diethyl ether (n-pentane : diethyl ether=3 : 1 by volume) to give 3.4 g of the desired compound of light yellow needle crystal (yield: 61.5%).

Workup

  1. customthe reaction
  2. concentrationthe reaction mixture was concentrated
  3. customto give precipitate
  4. washAfter washing the obtained precipitate with ether
  5. customthe precipitate was recrystallized from the mixture solution of n-pentane and diethyl ether (n-pentane : diethyl ether=3 : 1 by volume)

Sources & evidence

ORD record
ord-2eedc2a3bbdf4c7c9dc11c6c0e230689
Source dataset
uspto-grants-1992_10
Patent number
US05158963

Reaction notes

Loading…