Tetrahydrofuran → 2-(1H-Inden-2-yl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

Under nitrogen flow, a 1 L three-necked flask receives 400 mL of THF and 8 g of 2-chloromethylsilylindene and the mixture is cooled to −78° C. To this, 38.5 mL (38.5 mmol) of a solution (1.0M) of LiN(trimethylsilylene)2 in THF is added dropwise. After stirring at room temperature for 15 hours, the solvent is distilled off and the residue is extracted with 300 mL of hexane. The solvent was distilled off to obtain 2.2 g (6.4 mmol) of (1,2′-dimethylsilylene)(2,1′-dimethylsilylene) (indene) 2 (yield:33.4%). The results of 1H-NMR analysis (90 MHz, CDCl3) are as follows: δ-0.69, 0.73 (12H, dimethylsilylene), 3.66 (4H, —CH2—), 7.17 (8H, Ar—H).

Provenance & Evidence