Ethanol → HCID 19813400, compound

HRID 467126Notes

Reaction equation

HRID 467126 reaction equation
[C:1]([O:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=1)(=O)[CH2:2]C(C)=O.[C:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[C:30]([O-])(=O)[CH3:31].[NH4+:34].C([OH:37])C>>[C:26]([O:25][C:19]([C:20]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=2)[C:9]([C:8]([O:7][CH2:1][CH3:2])=[O:37])=[C:30]([CH3:31])[NH:34][C:21]=1[CH3:23])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 15538Tert-butyl acetoacetateHCID 517165Ammonium AcetateHCID 53832968HCID 53832968, compound

Product 1

HCID 19813400HCID 19813400, compoundYield 23.3%

Procedure

In 5 ml of ethyl alcohol was dissolved 1.95 g (0.008 mol) of 2 -(3-ethynylbenzylidene)-ethyl acetoacetate. Thereto were added 1.58 g (0.01 mol) of t-butyl acetoacetate, 0.77 g (0.01 mol) of ammonium acetate and 25 m: of ethyl alcohol. The admixture was reacted under reflux with heating for 1 hour. After completing the reaction, the reaction solution was distilled away under reduced pressure, the residue was purified by subjecting to silica gel column chromatography [eluent: n-hexane-ethyl acetate (7 : 1 to 5 : 1)] to give 0.7 g of the desired compound (yield: 23.3%).

Workup

  1. customThe admixture was reacted
  2. temperatureunder reflux
  3. temperaturewith heating for 1 hour
  4. customthe reaction
  5. distillationthe reaction solution was distilled away under reduced pressure
  6. customthe residue was purified

Sources & evidence

ORD record
ord-b42719368f64469c943d4bbd5d019f33
Source dataset
uspto-grants-1992_10
Patent number
US05158963

Reaction notes

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