Tributylstannane → Stannane, tributyl-1-cyclopenten-1-yl-

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (2.97 ml, 21.2 mmol) in dry tetrahydrofuran (140 ml) is added n-butyllithium (1.4 M in hexane) (15.3 ml, 21.4 mmol) drop wise at 0° C. and the resulting mixture stirred for 30 min. To the reaction mixture is then added tributylstannane (6.2 ml, 23.1 mmol) and stirring is continued for 30 min at 0° C. before cooling to −78° C. Cyclopentanone (2.1 ml, 23.8 mmol) in tetrahydrofuran (10 ml) is added and stirring is continued for 1 h at −78° C. Methanesulfonyl chloride (7.4 ml, 96.0 mmol) and triethylamine (24.9 ml, 179 mmol) are added successively to the reaction mixture at −78° C. The temperature of the reaction mixture is slowly raised to room temperature over a period of 1 h. Hexane (300 ml) is added and partitioned with acetonitrile (100 ml). The combined hexane layers are washed with acetonitrile (2×100 ml) and evaporated to get the crude product. Column chromatography (silica gel, hexane) afforded tributyl-1-cyclopenten-1-yl-stannane (6.1 g, 17.1 mmol, 72%).

Provenance & Evidence