Hydrochloric Acid → 4-{3-[(4-acetyl-3-fluorophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide

2,4-Difluoroacetophenone (0.40 g, 2.54 mmols), 4-{3-[(triisopropylsilyl)thio]phenyl}-tetra-hydro-2H-pyran-4-carboxamide (1.0 g, 2.54 mmols), tetrabutylammonium fluoride (0.66 g, 2.54 mmols), and potassium tert-butoxide (1.0 M in THF, 2.54 ml, 2.54 mmols) were added to anhydrous toluene (10 ml). The mixture was warmed to 90 degrees Celcius and stirred for 4 hours. After cooling to room temperature, ethyl acetate was added (100 ml) along with 1.0 N HCl (6 ml). The mixture was then stirred for 30 minutes and a beige precipate was collected by suction filtration. The crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone. The appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%).

1. temperatureThe mixture was warmed to 90 degrees Celcius
2. stirringThe mixture was then stirred for 30 minutes
3. filtrationa beige precipate was collected by suction filtration
4. customThe crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone
5. concentrationThe appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%)

ORDレコード

ord-5657c0da012f435683a36db2faaed799

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07772269B2