4-Toluenesulfonyl chloride → 1,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol

HRID 459422

反応式

HRID 459422 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:22])[C@H:13]1[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@@H:14]1[OH:15]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:21][CH2:20][C@H:18]2[O:19][C@H:13]([CH2:12][O:22][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[C@@H:14]([OH:15])[C@@H:16]2[OH:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 735442,5-anhydro-D-mannitol

生成物 1

HCID 140769161,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

5.33 g (27.945 mmol) of p-toluenesulphonyl chloride were added at 0° C. to a solution of 2.16 g (13.15 mmol) of 2,5-anhydro-D-mannitol in 88 ml of pyridine. The mixture was heated to room temperature and stirred for a further 24 hours. The reaction was hydrolysed using ice-water and extracted using CH2Cl2, and the combined organic phases were washed with 3N HCl and NaCl. After drying over MgSO4, the solvent was subsequently removed under reduced pressure. The crude product was purified by means of column chromatography (hexane/ethyl acetate 1:2). Yield: 3.00 g (48% of theory).

後処理

  1. extractionextracted
  2. washthe combined organic phases were washed with 3N HCl and NaCl
  3. dry with materialAfter drying over MgSO4
  4. customthe solvent was subsequently removed under reduced pressure
  5. customThe crude product was purified by means of column chromatography (hexane/ethyl acetate 1:2)

出典と根拠

ORDレコード
ord-0dd59ae4d97a4658b66d6ba2925c3377
出典データセット
uspto-grants-2007_03
特許番号
US07193092B2

関連ノート

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