Water → 3-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropane

HRID 440192ノート

反応式

HRID 440192 の反応式
Br[CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[Na+].O>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+]>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:2][CH2:3][CH2:4][O:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

参加物

7

反応物 3

HCID 962WaterHCID 2723791Sodium p-toluenesulfinateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

生成物 1

HCID 220761783-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropane収率 76%

試薬・触媒・溶媒 3

HCID 5238Sodium Iodide触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

32 g (144 mmol) of 3-bromo-1-tetrahydropyranyloxypropane (1a) are dissolved in 200 ml of 1,2-dimethoxyethane, 26.9 g (151 mmol) of anhydrous sodium 4-methylphenyl-sulfinate, 4.5 g (14 mmol) of tetrabutylammoniumbromide and 1.05 g (7 mmol) of sodium iodide are added and the mixture is heated to boiling for 24 hours. After cooling, 500 ml of water are added, the mixture is extracted with three times 300 ml of dichloromethane each time, the combined dichloromethane extracts are washed with water and dried with magnesium sulfate. After filtering off the drying agent and distilling off the solvent in vacuo a yellowish brown oil is obtained which is purified by column chromatography (silica gel; dichloromethane or dichloromethane/ethyl acetate mixtures). 32.5 g (76%) of a colorless oil are isolated, which partly crystallizes on prolonged standing (m.p.<30° C.)

後処理

  1. temperaturethe mixture is heated
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with three times 300 ml of dichloromethane each time
  4. washthe combined dichloromethane extracts are washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationdistilling off the solvent in vacuo a yellowish brown oil
  8. customis obtained which
  9. customis purified by column chromatography (silica gel; dichloromethane or dichloromethane/ethyl acetate mixtures)

出典と根拠

ORDレコード
ord-f8f90895a701458faf0af04f319daf24
出典データセット
uspto-grants-1996_05
特許番号
US05517350

反応ノート

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