Acetic Acid → Ethyl 2-(2-chlorophenyl)methylene-3-oxohexanoate

HRID 489401

반응식

HRID 489401 반응식
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[C:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 69962-ChlorobenzaldehydeHCID 8082PiperidineHCID 238498Ethyl 3-oxohexanoate

생성물 1

HCID 69733996Ethyl 2-(2-chlorophenyl)methylene-3-oxohexanoate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A solution of ethyl 3-ketohexanoate (7.5 g), 2-chlorobenzaldehyde (6.6 g), piperidine (1.2 g) and acetic acid (2.25 g) in benzene (50 ml) was heated under reflux for 5 hours, and the reaction mixture was dehydrated using a Dean-Stark condenser. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography using an eluent (hexane-ethyl acetate (3:1)) to give ethyl 2-(2-chlorophenyl)methylen-3-oxohexanoate ((E)/(Z)=1:1 mixture) as a yellow oil. A solution of ethyl 2-(2-chlorophenyl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture, 2.8 g), 3-amino-1-methylpyrazole (0.25 g) and p-toluenesulfonic acid (25 mg) in toluene (5 mL) and dimethylsulfoxide (0.5 mL) was heated under reflux for one day. The solvent was evaporated under reduced pressure, and the mixture was extracted with ethyl acetate (10 mL) and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give an oil. The obtained oil was purified by silica gel column chromatography (eluent (ethyl acetate-methanol (10:1))) to give the title compound as colorless crystals.

후처리

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a7f616313c3640079494d30a2742227c
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977262B2

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