2-Hexenoic acid, (2E)- → HCID 178445511、化合物

HRID 635136

反応式

HRID 635136 の反応式
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6].O[C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]34[CH2:29][CH2:28][C:25]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH2:26][CH2:27]3)[CH2:24][CH2:23]4)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:8][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]34[CH2:27][CH2:26][C:25]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH2:24][CH2:23]3)[CH2:28][CH2:29]4)=[CH:20][CH:21]=2)[CH2:12][CH2:11]1)(=[O:7])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6]

参加物

5

反応物 2

HCID 52827072-Hexenoic acid, (2E)-HCID 178442035HCID 178442035、化合物

生成物 1

HCID 178445511HCID 178445511、化合物収率 64.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of N,N-dicyclohexylcarbodiimide (0.22 g, 1.1 mmol) in dichloromethane (10 cm3) is added to a solution of (E)-hex-2-enoic acid (0.10 g, 0.9 mmol), 1-[4-(trans-4-hydroxycyclohexyl) phenyl]-4-pentylbicyclo[2.2.2]octane (0.32 g, 0.9 mmol), 4-(dimethylamino) pyridine (0.04 g) in dichloromethane (20 cm3), cooled in an ice bath (0° C.) under an atmosphere of nitrogen. The reaction mixture is stirred overnight, filtered to remove precipitated material and the filtrate is evaporated down under reduced pressure. The crude product is purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C.)/ethyl acetate mixture as eluent, followed by recrystallization from ethanol to yield the desired ester (0.26 g, 64%).

後処理

  1. filtrationfiltered
  2. customto remove
  3. customprecipitated material
  4. customthe filtrate is evaporated down under reduced pressure
  5. customThe crude product is purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C.)/ethyl acetate mixture as eluent
  6. customfollowed by recrystallization from ethanol

出典と根拠

ORDレコード
ord-4d60b3901e6844b7b4c3aa10eee24ce8
出典データセット
uspto-grants-2001_02
特許番号
US06187393B1

関連ノート

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