Ethyl Acetate → Cyclobutyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate

HRID 1789017Notes

Reaction equation

HRID 1789017 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[O:11]=[C:12]([CH3:21])[CH2:13][C:14]([O:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15].C(OCC)(=O)C>N1CCCCC1.C(O)(=O)CCCCC.C1C=CC=CC=1>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:13]([C:12](=[O:11])[CH3:21])[C:14]([O:16][CH:17]1[CH2:18][CH2:19][CH2:20]1)=[O:15]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 357452,3-DichlorobenzaldehydeHCID 20189390Cyclobutyl 3-oxobutanoate

Product 1

HCID 54003830Cyclobutyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 8892Hexanoic AcidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2,3-dichlorobenzaldehyde (1.57 g, 8.9 mmoles), cyclobutyl 3-oxobutanoate (1.4 g, 8.9 mmoles), piperidine (8 drops) and hexanoic acid (11 drops) in dry benzene (100 ml) was heated at reflux for 12 hours using a Dean and Stark apparatus. The solution was allowed to cool to room temperature and the solvent removed in vacuo to leave the crude sub-title compound as an oil 3.5 g. Chromatography on silica eluting with petroleum ether (60°-80° )/ethyl acetate mixtures afforded the sub-title compound as an oil, 1.7 g.

Workup

  1. temperatureat reflux for 12 hours
  2. customthe solvent removed in vacuo
  3. customto leave the crude sub-title compound as an oil 3.5 g

Sources & evidence

ORD record
ord-40d2eb20fccb43b288debf4e7f21a1c3
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

Loading…