2-Hexenoic acid, (2E)- → 2-[4-(4-Pentylbicyclo[2.2.2]octyl)phenyl]pyrimidin-5-yl (e)-hex-2-enoate

HRID 635139

反応式

HRID 635139 の反応式
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6].O[C:10]1[CH:11]=[N:12][C: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)=[N:14][CH:15]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:8][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:17]=[CH:18][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:20][CH:21]=2)=[N:14][CH:15]=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 212577621-[4-(5-Hydroxypyrimidin-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane

生成物 1

HCID 1317223792-[4-(4-Pentylbicyclo[2.2.2]octyl)phenyl]pyrimidin-5-yl (e)-hex-2-enoate収率 45%

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-(5-hydroxypyrimidin-2-yl) phenyl]-4-pentylbicyclo[2.2.2]octane (0.25 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 recrystallisation from ethanol to yield the desired ester (0.15 g, 45%).

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 recrystallisation from ethanol

出典と根拠

ORDレコード
ord-f5ac0fc0e46847b6b8a50de7c2e2ee59
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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