Reaktion #50761

Reaktionsgleichung

2-(3,4,dimethoxybenzyl)-5-methoxytetrahydrofuran

benzenesulphinic acid

calcium chloride

→

2-benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran

Ausbeute 36.2%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched
2. 2
   Waschenby washing with water (2×50 ml)
3. 3
   Trocknendried over anhydrous sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeColumn chromatography (flash silica gel; 3:2 hexane/ethyl acetate) provided the product (Rf 0.3) as a clear oil which
7. 7
   Sonstigewas crystalized from ethyl acetate/hexane

Vorschrift

To a solution of benzenesulphinic acid (8.68 g, 0.061M) in DCM (120 ml) containing a suspension of powdered calcium chloride (1.0 g) at room temperature was added a solution of 2-(3,4,dimethoxybenzyl)-5-methoxytetrahydrofuran (7.0 g, 0.029M) in DCM (80 ml). The mixture was stirred at room temperature for 4 h, quenched by washing with water (2×50 ml), dried over anhydrous sodium sulphate, filtered and evaporated. Column chromatography (flash silica gel; 3:2 hexane/ethyl acetate) provided the product (Rf 0.3) as a clear oil which was crystalized from ethyl acetate/hexane to give 2-benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran (3.5 g, 35%).

Quelle