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

HRID 477009ノート

反応式

HRID 477009 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a58846be46a041d9acbe04c68d658a67
出典データセット
uspto-grants-1989_12
特許番号
US04886817

反応ノート

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