Water → (E)-1-phenyl-8-p-toluenesulfonyloxy-2-octene

HRID 477009노트

반응식

HRID 477009 반응식
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O.CCOCC>N1C=CC=CC=1>[C:1]1([CH2:7]/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 14834222(E)-8-phenyl-7-octen-1-ol

생성물 1

HCID 19837249(E)-1-phenyl-8-p-toluenesulfonyloxy-2-octene수율 91.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
10 °C

실험 절차

To a solution of 7.5 g of (E)-8-phenyl-7-octen-1-ol dissolved in 60 ml of pyridine, 9.1 g of p-toluenesulfonyl chloride was added at 0° C. After stirring at 10° C. for 5 hours, 10 ml of water was added and the mixture was stirred for 30 minutes, followed by addition of 200 ml of ether. The mixture was washed with 10% aqueous hydrochloric acid, water and saturated saline water. The organic layer was dried, and the solvent was removed under reduced pressure. The pale yellow oily product obtained was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=5:1) to give 12 g of (E)-1-phenyl-8-p-toluenesulfonyloxy-2-octene as an oily product.

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. washThe mixture was washed with 10% aqueous hydrochloric acid, water and saturated saline water
  3. customThe organic layer was dried
  4. customthe solvent was removed under reduced pressure
  5. customThe pale yellow oily product obtained
  6. customwas purified by silica gel column chromatography (solvent: hexane-ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-a58846be46a041d9acbe04c68d658a67
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886817

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