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

HRID 459422

반응식

HRID 459422 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0dd59ae4d97a4658b66d6ba2925c3377
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07193092B2

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