Diethyl Ether → HCID 22731984, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-chloro-8-difluoromethoxy-4-thiochromanone (2.5 g, 9.40 mmol; from step (iii) above) in anhydrous Et2O (150 mL) was cooled to 0° C. under nitrogen. Tebbe Reagent (21.0 mL of 0.5M in toluene, 10.3 mmol) was added dropwise via syringe, and the mixture was stirred at 0° C. for 2 h and then stirred at room temperature for 1 h. The reaction was cooled to 0° C. and slowly quenched with MeOH (ca. 50 mL) until the solution solidified. The mixture was diluted with EtOAc/H20 (4:1, 100 mL) and filtered through a pad of Celite. The Celite was washed with EtOAc (800 mL) and the filtrate was concentrated in vacuo. The crude dark red oil was chromatographed on silica gel eluting with Hex:EtOAc (4:1) to afford 0.88 g (36%) of sub-title compound as a dark yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.40 (s, 1H), 7.05 (s, 1H), 6.46 (t, J=75 Hz, 1H), 5.53 (s, 1H), 5.10 (s, 1H), 3.06 (t, J=7.5 Hz, 2H), 2.80 (t, J=7.5 Hz, 2H).

Provenance & Evidence