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

HRID 1464483Notes

Reaction equation

HRID 1464483 reaction equation
[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

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22851377HCID 22851377, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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,

Workup

  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,

Sources & evidence

ORD record
ord-0550ec449d864ed99fdc42c3a4ed149e
Source dataset
uspto-grants-1994_04
Patent number
US05304687

Reaction notes

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