Water → HCID 178444549、化合物

HRID 370683

反応式

HRID 370683 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]#[N:11])=[CH:4][CH:3]=1.[CH2:12]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23](O)=[O:24])[CH2:19][CH2:18]1)[CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:10]([C:9]#[C:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:23]([C@H:20]2[CH2:21][CH2:22][C@H:17]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19]2)=[O:24])=[CH:7][CH:6]=1)#[N:11]

参加物

7

反応物 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 20274918(p-Hydroxyphenyl)propiolonitrileHCID 178444557HCID 178444557、化合物

生成物 1

HCID 178444549HCID 178444549、化合物収率 84%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 143 mg of (p-hydroxyphenyl)propiolonitrile, 218 mg of trans-4-pentylcyclohexanecarboxylic acid, 227 mg of N,N'-dicyclohexylcarbodiimide and 12.2 mg of 4-(dimethylamino)pyridine in 15 ml of methylene chloride was stirred at room temperature for 105 minutes in a round flask under argon gasification. The yellow heterogeneous mixture was subsequently poured into 30 ml of water and extracted twice with 30 ml of methylene chloride each time. The organic phases were washed in sequence twice with 30 ml of water each time, twice with 30 ml of 5% acetic acid each time and twice with 30 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.4 bar) of the residue (383 mg) on silica gel with 3% ethyl acetate/petroleum ether gave 270 mg (84%) of trans-4-pentylcyclohexanecarboxylic acid p-(2-cyanoethynyl)phenyl ester as colourless crystals. A single crystallization from hexane yielded 219 mg of the ester as colourless platelets (purity 99.7%); m.p. (C-N) 76.8° C., cl.p. (N-I) 153.2° C.

後処理

  1. extractionextracted twice with 30 ml of methylene chloride each time
  2. washThe organic phases were washed in sequence twice with 30 ml of water each time
  3. dry with materialtwice with 30 ml of 5% acetic acid each time and twice with 30 ml of water each time, dried over magnesium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-38c60b64aa0949c08629c70e827ec75f
出典データセット
uspto-grants-1985_07
特許番号
US04528114

関連ノート

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