Water → HCID 178444549, 화합물

HRID 370683

반응식

HRID 370683 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 20274918(p-Hydroxyphenyl)propiolonitrileHCID 178444557HCID 178444557, 화합물

생성물 1

HCID 178444549HCID 178444549, 화합물수율 84%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-38c60b64aa0949c08629c70e827ec75f
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04528114

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