Benzene → Trans-4-(acetylthio)-2-phenyl-1,3-dioxane

HRID 381417ノート

反応式

HRID 381417 の反応式
[C:1]1([C@H:7]2[O:12][C@@H:11](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O-:27])(=[S:26])[CH3:25].[Na+].C1C=CC=CC=1>CN(C)C=O>[C:24]([S:26][C@@H:11]1[CH2:10][CH2:9][O:8][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:12]1)(=[O:27])[CH3:25]

参加物

5

反応物 3

HCID 241BenzeneHCID 23700354HCID 23700354、化合物HCID 86583790cis-2-Phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane

生成物 1

HCID 86583806Trans-4-(acetylthio)-2-phenyl-1,3-dioxane収率 43.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
117.5 °C

実験手順

In 200 ml of dimethylformamide were dissolved 29.0 g (86.8 mmol) of cis-2-phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane and 17.0 g (149 mmol) of sodium thioacetate, and the solution was heated at 115 to 120° C. under a nitrogen atmosphere for 1 hour. After cooling, benzene was added to the reaction mixture and the mixture was washed with water, followed by evaporation of the solvent. The thus obtained brown residue was subjected to column chromatography using silica gel and the fractions eluted with a mixed solvent of benzene-hexane (2:1) were collected, followed by recrystallization from a mixed solvent of benzene-hexane to obtain 8.99 g (yield: 43%) of the title compound having a melting point of 95 to 96° C.

後処理

  1. temperatureAfter cooling
  2. washthe mixture was washed with water
  3. customfollowed by evaporation of the solvent
  4. washthe fractions eluted with a mixed solvent of benzene-hexane (2:1)
  5. customwere collected
  6. customfollowed by recrystallization from a mixed solvent of benzene-hexane

出典と根拠

ORDレコード
ord-a4f5c64bc10e4ceabe13d7d6b868c92e
出典データセット
uspto-grants-2001_10
特許番号
US06306880B1

反応ノート

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