Water → HCID 69025373, compound

Participants

Reaction Conditions

Reaction Steps

2-bromo-3-methoxy-1,3-dimethyl-cyclopentene (5 g, 24.38 mmol) was dissolved in 30 ml of diethylether and the reactant solution was cooled to −30° C. using a Schlenk line in a nitrogen atmosphere. Then, n-butyllithium (6.67 g) was added and the resultant solution was incubated at an elevated temperature for 15 minutes until a white solid was obtained and then again cooled to −30° C. 1 eq. (3.14 g) of Me2SiCl2 was added and the resultant solution was incubated for 5 hours while gradually being heated to room temperature. Then, NaCp (12.5 ml, 25.0 mmol, 2M in THF) was added to the first reactor preset to −30° C. and the resultant solution was incubated at room temperature for 5 hours or more. 20 ml of water and 20 ml of ethylacetate were added thereto and an aqueous layer was once Washed with 20 ml of ethylacetate and then stirred with 50 ml of 1 N HCl for 3 minutes. The resultant solution was neutralized with 50 ml of a saturated sodium bicarbonate solution, and subjected to solvent removal in a rotary evaporator and then to water removal using magnesium sulfate. Finally, the residue was purified by silica-based column chromatography (hexane), to give (2,5-dimethyl-cyclopenta-1,4-dienyl)(cyclopenta-1,4-dienyl)-dimethylsilane (yield: 66%).

Provenance & Evidence