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

HRID 635139

반응식

HRID 635139 반응식
[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]

참가 물질

5

반응물 2

HCID 52827072-Hexenoic acid, (2E)-HCID 212577621-[4-(5-Hydroxypyrimidin-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f5ac0fc0e46847b6b8a50de7c2e2ee59
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187393B1

연결된 노트

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