Ethyl acetate hexane → HCID 53753365, compound

HRID 496823Notes

Reaction equation

HRID 496823 reaction equation
C[O:2][C:3](OC)([C:5]([C:13]#[N:14])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:4].CCCCCC.C(OCC)(=O)C>Cl>[C:13]([C:5](=[CH:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:3](=[O:2])[CH3:4])#[N:14]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 54116840HCID 54116840, compound

Product 1

HCID 53753365HCID 53753365, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A sample of 3-cyano-4-phenyl-3-buten-2-one dimethylketal, prepared in accordance with the procedure of Example 5 (5.0 g, 23 mmol) was suspended in 6N HCl (100 mL) and stirred at room temperature for 72 h1. Thin layer chromatographic analysis (SiO2, hexane—ethyl acetate 7:3) indicated nearly complete conversion of the ketal to the lower Rf ketone which had deposited along the bottom of the reaction flask as a yellow solid. The solid was purified by column chromatography (SiO2, hexane—ethyl acetate 9:1) and the desired fractions evaporated to give 1.5 g (38%) of 3-cyano-4-phenyl-3-buten-2-one, as colorless needles, mp 83-84° C. (lit. 80-81° C.2).

Workup

  1. customThe solid was purified by column chromatography (SiO2, hexane—ethyl acetate 9:1)
  2. customthe desired fractions evaporated

Sources & evidence

ORD record
ord-36a4cd53eefa4406b6250347119a87df
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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