HCID 59523110, compound → HCID 59523108, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6.24 g (14.7 mmol) of compound 11 in 150 mL of THF was cooled to −78° C. and treated dropwise with 6.45 mL (16.1 mmol) of n-BuLi (2.5 M in hexanes). The mixture was stirred for 45 minutes, then the dry ice bath was removed and the mixture was stirred at ambient temperature for 1 hour. The mixture was cooled to 0° C. and treated with 5.69 g (16.1 mmol) of Fe(acac)3 (Strem Chemicals, Inc.). The mixture was heated in an 80° C. oil bath for 2 h, cooled to room temperature, and filtered. The filter cake was washed with 3×25 mL of THF. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, 5.5×35 cm, chloroform) to give 6.0 g (96% yield) of compound 12 as a yellow oil. 1H NMR (500 MHz) δ 4.51 (t, 4H, J=6.3 Hz), 1.86-0.88 (m, 88H).

Provenance & Evidence