Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile

HRID 1951394노트

반응식

HRID 1951394 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].C(O)(=O)C.N1CCCCC1>ClCCl.C1CCCCC1.C(OCC)(=O)C>[C:15]([C:14]([C:13](=[O:18])[CH3:12])=[CH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1])(=[O:17])[CH3:16]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 122905503-Chloro-4-formylbenzonitrile

생성물 1

HCID 674168404-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile수율 89.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 21867204Cyclohexane ethylacetate용매

실험 절차

300 mg (1.812 mmol) of 3-chloro-4-formylbenzonitrile, 181.4 mg (1.812 mmol) of 2,4-pentanedione, 163.2 mg (2.72 mmol) of acetic acid and 30.9 mg (0.36 mmol) of piperidine are dissolved in 15 ml of dichloromethane and heated under reflux with an inverse water trap overnight. The mixture shows complete conversion (TLC check, mobile phase: cyclohexane/ethyl acetate 5:1). The mixture is diluted with dichloromethane, washed with water and saturated sodium chloride solution and dried with sodium sulfate. The solvent is removed in a rotary evaporator. 403 mg (89.8% of theory) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile are obtained and are reacted without further purification.

후처리

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customThe solvent is removed in a rotary evaporator

출처 및 근거

ORD 기록
ord-8344fbcb2ebf436692eb2bcd4f9543bb
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404709B2

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