Dimethyl Sulfoxide → HCID 22393676, compound

Temperature

-55 °C

Oxalyl chloride (0.70 ml) was dissolved in methylene chloride (10 ml), and then the mixture was cooled to −60 to −50° C. Dimethyl sulfoxide (0.57 ml) was added thereto, and the mixture was stirred for 2 minutes. Further, a methylene chloride solution (6 ml) of 3-cyano-5-(1-hydroxy-2-methylpropyl)thiophene (1.21 g) was added thereto at −60 to −50° C., and the mixture was stirred for 15 minutes. Then, triethylamine (4.65 ml) was added, and the temperature of the mixture was raised to a room temperature. Ethyl acetate was added, and the mixture was washed with water and further brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was recrystallized from ethanol, to give the title compound as pale yellowish white crystals (0.59 g) Further, the filtrate was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound (0.41 g, total yield: 1.00 g, 84%).

1. stirringat −60 to −50° C., and the mixture was stirred for 15 minutes
2. temperaturethe temperature of the mixture was raised to a room temperature
3. washthe mixture was washed with water and further brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customevaporated
6. customThe resulting residue was recrystallized from ethanol

ORD record

ord-4fedc1da025048579655b4f04e1ae6bc

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06906072B1