Ammonium Chloride → HCID 86218651, compound

Temperature

-30 °C

6,7-Dihydrobenzo[b]thiophen-4(5H)-one (8.48 g, 56 mmol) was dissolved in anhydrous diethyl ether (200 mL) and the solution was cooled to −30° C. Vinyl magnesium chloride (60 mL, 1.6 M solution in THF, 96 mmol) was added to the ketone portion-wise whilst maintaining the temperature at −30° C. Upon completion of the addition, the reaction was stirred at −30° C. for 30 min and then allowed to warm to 25° C. Stirring was continued overnight and the solution was then treated with saturated ammonium chloride solution. The product was extracted into dichloromethane and this was back extracted with water and saturated brine. The dichloromethane solution was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a crude, yellow oil (10.1 g, 100%). This compound was used directly in the next step without further purification.

1. temperaturewhilst maintaining the temperature at −30° C
2. additionUpon completion of the addition
3. temperatureto warm to 25° C
4. stirringStirring
5. waitwas continued overnight
6. extractionThe product was extracted into dichloromethane
7. extractionthis was back extracted with water and saturated brine
8. dry with materialThe dichloromethane solution was dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-066a5744eefb437fae1f1c548993669e

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233982B2