Dicyclohexylcarbodiimide → HCID 178455793、化合物

HRID 370702ノート

反応式

HRID 370702 の反応式
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)#[CH:2].[CH2:12]([C@H:17]1[CH2:22][CH2:21][C@H:20](O)[CH2:19][CH2:18]1)[CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:12]([C@H:17]1[CH2:18][CH2:19][C@H:20]([O:10][C:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([C:1]#[CH:2])[CH2:4][CH2:5]2)=[O:11])[CH2:21][CH2:22]1)[CH2:13][CH2:14][CH2:15][CH3:16]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 178444573HCID 178444573、化合物HCID 178455788HCID 178455788、化合物

生成物 1

HCID 178455793HCID 178455793、化合物収率 65.1%

試薬・触媒・溶媒 2

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

実験手順

A mixture of 122 mg of trans-4-ethynylcyclohexanecarboxylic acid, 145 mg of trans-4-pentylcyclohexanol, 206 mg of dicyclohexylcarbodiimide and 12.2 mg of 4-(dimethylamino)pyridine in 10 ml of methylene chloride was stirred at room temperature for 21 hours. The separated white precipitate was filtered off, the filtrate was poured into 50 ml of water and extracted three times with 50 ml of methylene chloride each time. The organic phases were washed once with 50 ml of water, twice with 30 ml of 5% aqueous acetic acid each time and twice with 30 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue on silica gel with 5% ethyl acetate/petroleum ether gave 159 mg (65%) of trans-4-ethynylcyclohexanecarboxylic acid trans-4-pentylcyclohexyl ester as a colourless crystallizing oil. Additional crystallization from isopropanol at -20° C. yielded and analytically pure ester; m.p. (C-I) 54.2° C., cl.p. (N-I) 40.5° C.

後処理

  1. filtrationThe separated white precipitate was filtered off
  2. additionthe filtrate was poured into 50 ml of water
  3. extractionextracted three times with 50 ml of methylene chloride each time
  4. washThe organic phases were washed once with 50 ml of water, twice with 30 ml of 5% aqueous acetic acid each time
  5. dry with materialtwice with 30 ml of water each time, dried over magnesium sulphate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-723eac23960640cb82332e69264bfe48
出典データセット
uspto-grants-1985_07
特許番号
US04528114

反応ノート

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