3-(Tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-trityloxymethyl-cyclopentanone → 4-(Tert-butyl-diphenyl-silanyloxy)-2-methylene-3-trityloxymethyl-cyclopentanol

Participants

Reaction Conditions

Reaction Steps

2.4 ml (1.26 mmol) of 20% suspension Nysted reagent and 6.4 ml of tetrahydrofuran were added dropwise to a reactor successively and cooled to 0° C. 0.14 ml (1.26 mmol) of TiCl4 was added thereto dropwise, and the resulting mixture was stirred. The reaction mixture was cooled to −40° C., and a solution which had been prepared by dissolving 0.527 g (0.842 mmol) of 3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-trityloxymethyl-cyclopentanone (a compound of formula (2)) obtained in Example 2 in 2.4 ml of tetrahydrofuran was added thereto. The reaction mixture was stirred at room temperature for 3.5 hrs. After completion of the reaction, the reaction mixture was cooled to −20° C., quenched by adding 25 ml of 1N hydrochloric acid, and extracted with 25 ml of dichloromethane to separate an organic layer. The organic layer was washed with 20 ml of 4% sodium bicarbonate solution and 20 ml of brine successively, dried over anhydrous sodium sulfate, filtered, and condensed. The residue thus obtained was isolated by HPLC to obtain 0.184 g of the title compound (yield: 50%).

Provenance & Evidence