Реакция #50761

Уравнение реакции

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

benzenesulphinic acid

calcium chloride

→

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

Выход 36.2%

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   Другоеquenched
2. 2
   Промывкаby washing with water (2×50 ml)
3. 3
   Сушкаdried over anhydrous sodium sulphate
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated
6. 6
   ДругоеColumn chromatography (flash silica gel; 3:2 hexane/ethyl acetate) provided the product (Rf 0.3) as a clear oil which
7. 7
   Другоеwas crystalized from ethyl acetate/hexane

Методика

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%).

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