Reaktion #63769

Reaktionsgleichung

sodium bicarbonate

dimethylaminopyridine

methanesulfonyl chloride

4-(3-t-butyldimethylsiloxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)-2-cyclopentenone

→

4-(3-t-butyldimethylsilyloxy-1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone

Ausbeute 25.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with a saturated aqueous solution of sodium chloride
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   FiltrationThe dried product was filtered
4. 4
   Einengenconcentrated

Vorschrift

480 mg (1.0 mmole) of 4-(3-t-butyldimethylsiloxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)-2-cyclopentenone was dissolved in 5 ml of dichloromethane, followed by addition of 730 mg (6 mmoles) of dimethylaminopyridine and 230 microliters (3.0 mmoles) of methanesulfonyl chloride in this order. The mixture was stirred at 40° C. for 2 hours. An aqueous solution of sodium bicarbonate was added, and the mixture was stirred with dichloromethane. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel 20 g; eluent, hexane:ethyl acetate=10:1) to give 114 mg (yield 25%) of 4-(3-t-butyldimethylsilyloxy-1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone. The resulting compound had the following spectral data.

Quelle