Water → 4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-yl methanesulfonate
Reaktionsgleichung
[Si:1]([O:8][CH2:9][C:10]#[C:11][CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(OCC)(=O)C>[CH3:21][S:22]([O:13][CH2:12][C:11]#[C:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:24])=[O:23]Komponenten
6
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-ol (701.4 mg) was dissolved in ethyl acetate (15 mL), and the solution was cooled to 0° C. Triethylamine (1.1 mL) and methanesulfonyl chloride (0.3 mL) were added, and the mixture was stirred at 0° C. for 3 hrs. Water was added to the reaction mixture and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50) to give the title compound (469.7 mg) as a colorless oil.
Aufarbeitung
- extractionthe mixture was extracted with diethyl ether
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was separated
- custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50)
Quellen und Nachweise
- ORD-Eintrag
- ord-f67e0c5573474a96a6a9e38a940f11f0
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08178543B2
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