Thionyl Chloride → 2-[Chloro(cyclohexyl)methyl]-3-methyl-1-benzofuran-5-carbonitrile

To a solution (10 mL) of 2-[cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrile (922 mg) synthesized above in toluene was added thionyl chloride (374 μL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (868 mg, 88%) as a pale-yellow solid.

1. additionThe reaction mixture was poured into ice-
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-ef9ed030a8c849e79e168eb6154af4ef

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2