Diethyl Ether → HCID 22731984, compound

Temperature

0 °C

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).

1. stirringstirred at room temperature for 1 h
2. temperatureThe reaction was cooled to 0° C.
3. customslowly quenched with MeOH (ca. 50 mL) until the solution
4. additionThe mixture was diluted with EtOAc/H20 (4:1, 100 mL)
5. filtrationfiltered through a pad of Celite
6. washThe Celite was washed with EtOAc (800 mL)
7. concentrationthe filtrate was concentrated in vacuo
8. customThe crude dark red oil was chromatographed on silica gel eluting with Hex

ORD record

ord-738a704d69824c0f977cb315cee0b41a

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716834B2