Thionyl Chloride → 4-{4-[chloro(cyclohexyl)methyl]-5-ethylthiophen-2-yl}tetrahydro-2H-pyran

To a solution of cyclohexyl[2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophen-3-yl]methanol (737 mg) synthesized above in toluene (10 mL) was added thionyl chloride (209 μL), and the mixture was stirred at room temperature for 2 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 compound (725 mg, 93%) as a pale-yellow oil.

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-Eintrag

ord-b1dfb88ac3d24423a66b015034c3b187

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08309580B2