Reaktion #58674

Reaktionsgleichung

methyl methylsulfonylacetate

1,3-diiodopropane

cesium carbonate

→

methyl 1-methylsulfonylcyclobutanecarboxlate

Ausbeute 79.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was partitioned between water (50 mL) and ethyl acetate (100 mL)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to dryness
6. 6
   Sonstigethe residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane

Vorschrift

To a solution of methyl methylsulfonylacetate (1.0 g, 6.6 mmol) in 20 mL of acetonitrile was added 1,3-diiodopropane (2.3 mL, 20 mmol) and cesium carbonate (6.4 g, 20 mmol). After stirring at room temperature for 2 h, the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane to give methyl 1-methylsulfonylcyclobutanecarboxlate (1.0 g, 79%). δ 3.84 (s, 3H), 3.02 (s, 3H), 2.84-2.65 (m, 4H), 2.25-2.02 (m, 2H).

Quelle