4-Toluenesulfonyl chloride → (2S)-2-Methoxy-2-{2-[(4-methylbenzene-1-sulfonyl)oxy]ethoxy}ethyl 4-methylbenzene-1-sulfonate

HRID 1464483노트

반응식

HRID 1464483 반응식
[OH:1][CH2:2][C@@H:3]([O:8][CH3:9])[O:4][CH2:5][CH2:6][OH:7].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:1][CH2:2][C@@H:3]([O:8][CH3:9])[O:4][CH2:5][CH2:6][O:7][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])(=[O:18])=[O:17])=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 22851377HCID 22851377, 화합물

생성물 1

HCID 71711110(2S)-2-Methoxy-2-{2-[(4-methylbenzene-1-sulfonyl)oxy]ethoxy}ethyl 4-methylbenzene-1-sulfonate수율 62%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

1,5-dihydroxy-2(S)-methoxy-3-oxa-pentane (E4) (1.4 g, 10.3 mmole), prepared as described in Example 8, was dissolved in dry pyridine (10 ml) and treated at 0° C. with p-toluensulfonylchloride (6.4 g, 0.034 mole). The mixture was kept at 4° C. overnight, then was poured into an ice-water mixture and finally extracted with methylene chloride. The organic phase was washed with water, separated off, dried over anhydrous sodium sulphate, filtered off. The solvent was removed under reduced pressure. The crude material was chromatographed on a silicic acid column using methylene chloride as eluting agent to give 2.8 g (yield 62%) of pure title derivative,

후처리

  1. extractionfinally extracted with methylene chloride
  2. washThe organic phase was washed with water
  3. customseparated off
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered off
  6. customThe solvent was removed under reduced pressure
  7. customThe crude material was chromatographed on a silicic acid column
  8. washas eluting agent
  9. customto give 2.8 g (yield 62%) of pure title derivative,

출처 및 근거

ORD 기록
ord-0550ec449d864ed99fdc42c3a4ed149e
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304687

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