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

HRID 1601354ノート

反応式

HRID 1601354 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-c7063ae59e01435ebc46b26e406f019e
出典データセット
uspto-grants-1999_11
特許番号
US05977152

反応ノート

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