Methanesulfonyl chloride → HCID 15391547, Verbindung

HRID 399682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399682
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH2:26][CH2:27][OH:28])[CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.CCOCC>[CH3:29][S:30]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH2:26][CH2:27][O:28][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:7][O:8][Si:9]([C:22]([CH3:24])([CH3:23])[CH3:25])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:32])=[O:31]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 187904721-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane

Produkt 1

HCID 15391547HCID 15391547, VerbindungAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred CH2Cl2 (400 mL) solution of diol, 1-(2-hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane (5.48 g, 13.6 mmol) under N2 atmosphere was added TEA (11.2 mL, 78 mmol), followed by dropwise addition of methane sulfonyl chloride (3 mL, 39.00 mmol) in CH2Cl2 (100 mL) over a period of 30 minutes. After 12 hours, the reaction was diluted with ether (500 mL), washed with water (100 mL×3), brine (100 mL), dried, and concentrated under reduced pressure to a residue. The residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent gave the bismesylate, 1-(2-(methylsulfonyloxy)-ethoxy)-2-((methylsulfonyloxy)ethyl)-3-(tert-butyldiphenylsilyloxy)-propane (7.40 g, 97%). Rf =0.55 (50% ethyl acetate in hexane). NMR. ##STR24##

Aufarbeitung

  1. washwashed with water (100 mL×3), brine (100 mL)
  2. customdried
  3. concentrationconcentrated under reduced pressure to a residue
  4. washThe residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-a9635bc8dbc144feb31fb741c39b4292
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821365

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