Diethyl Ether → 2-ethyl-1h-indene

Participants

Reaction Steps

2-Bromoindene (8.1235 g, 0.04211 moles) and Ni(dppp)Cl2 (0.1536 g, 2.83×10-4 moles) were stirred in diethylether (100 mL) at -78° C. under a nitrogen atmosphere as ethylMgBr (0.045 moles, 15.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution and then back to the heterogeneous brick-red mixture during the course of the warm-up. Gas chromatographic analysis after 2 hours of stirring at room temperature showed that the reaction was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1×100 mL) and 1 M NaHCO3 (1×100 mL) and then dried with MgSO4 and filtered. The desired product was isolated as a light yellow oil (5.65 g, 93.1 percent).

Provenance & Evidence