Hydrochloric Acid → HCID 178506815, compound

Participants

Reaction Conditions

Reaction Steps

In Example 5, 3H-1-(but-3-enyl)indene was prepared. About 100 mL of a 2 M solution of allylmagnesium chloride in THF was added to a solution of 13 mL of bromochloromethane (200 mmol) in 50 mL of THF. This mixture was refluxed for 3 hr and then stirred for 14 hr. A solution of indenyl lithium was prepared from 30 mL of 90% indene (232 mmol) and 85 mL of 2.5 M n-butyllithium in 100 mL of THF. This solution was then added by cannula to the mixture over 1 hr, and the resulting mixture was refluxed for 6 hr. Then, the mixture was poured into 200 mL of 1M HCl, followed by extraction with 100 mL of pentane. The extract was washed with 3×100 mL of water, dried over sodium sulfate and concentrated with a rotary evaporator while heating to 30° C. The residue was distilled through a 6-inch 14/20 Vigreux column at 0.01 mm Hg, and product collected at 79-80° C. Next, the product was evacuated to further remove light materials. The resulting indene material contained greater than 90% butenylindene.

Provenance & Evidence