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

HRID 1601354노트

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HRID 1601354 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
117.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7063ae59e01435ebc46b26e406f019e
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977152

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