Tetrahydrofuran → HCID 68327457, compound

Participants

Reaction Steps

A suspension of zinc dust (1300 mg, 20 mmol), LiCl (420 mg, 10 mmol), I2 (10 mg), dibromoethane (50 mg) in THF (20 mL) was heated to reflux for 15 min. and then treated with 4-methoxybenzyl chloride (16) (1.56 g, 10 mmol). Heating was continued for 6 h and the suspension was then cooled to rt before being treated (Ph3P)2NiCl2 (50 mg). The resulting red suspension was treated with 4 (1.56 g, 10 mmol) and the mixture was stirred for an extra 10 min. before being washed with NH4Cl and saturated NaHCO3. The organic layer was evaporated under reduced pressure to afford a pale yellow oil (3.03 g, 94%), which was found to be pure 17 by NMR. 1H NMR (300 MHz, CDCl3) δ ppm 9.01 (s, 1H), 8.55 (s, 2H), 7.95 (d, 2H), 7.39 (d, 2H), 4.12 (s, 2H), 3.52 (s, 3H).

Provenance & Evidence