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

HRID 1951394ノート

反応式

HRID 1951394 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 21867204Cyclohexane ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8344fbcb2ebf436692eb2bcd4f9543bb
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

反応ノート

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