Dimethylformamide → HCID 59888900, compound

6,7-Dihydrobenzo[b]thiophen-4(5H)-one (1.0 g, 6.6 mmol) in toluene (10 mL) was added drop-wise to NaH (60% dispersion in mineral oil, 1.32 g, 32.9 mmol) in toluene (5 mL). DMF (5 mL) was added and the reaction was stirred at room temperature for 1 hr. The mixture was cooled to 0° C., methyl iodide (4.67 g, 2.1 mL, 32.9 mmol) was added drop-wise and the solution was refluxed for 3 h. The mixture was cooled and carefully treated with iso-propanol. The product was extracted into diethyl ether (×3) and this was back extracted with water and saturated brine. The diethyl ether solution was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified on silica gel using a gradient elution of 0-75% ethyl acetate in 40-60 petroleum ether to afford the title compound as a yellow oil (0.375 g, 32%).

1. temperatureThe mixture was cooled to 0° C.
2. temperaturethe solution was refluxed for 3 h
3. temperatureThe mixture was cooled
4. extractionThe product was extracted into diethyl ether (×3)
5. extractionthis was back extracted with water and saturated brine
6. dry with materialThe diethyl ether solution was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified on silica gel using
10. washa gradient elution of 0-75% ethyl acetate in 40-60 petroleum ether

ORD record

ord-d2902c0c4ea9443896fc08c0af7bb316

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233982B2