2-Hexenoic acid, (2E)- → HCID 178445511, 화합물

HRID 635136

반응식

HRID 635136 반응식
[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]

참가 물질

5

반응물 2

HCID 52827072-Hexenoic acid, (2E)-HCID 178442035HCID 178442035, 화합물

생성물 1

HCID 178445511HCID 178445511, 화합물수율 64.1%

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-(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%).

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 recrystallization from ethanol

출처 및 근거

ORD 기록
ord-4d60b3901e6844b7b4c3aa10eee24ce8
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187393B1

연결된 노트

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