Sodium hydride → 5-{7-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran-5-yl}pyrimidine

To a solution of 1,1,1-trifluoro-4-methyl-4-(5-pyrimidin-5-yl-2,3-dihydrobenzofuran-7-yl)pentan-2-one (620 mg, 1.8 mmol) in 5 mL of anhydrous DMSO-THF (1:1) was added 2.64 mL of a trimethylsulfoxonium ylide solution (stock solution prepared by reaction of NaH (242 mg, 60% dispersion in mineral oil) with trimethylsulfoxonium iodide (1.33 g, 6.0 mmol) in 7.50 mL of anhydrous DMSO for 30 minutes) dropwise over 5 minutes. After stirring for 2 hour at room temperature, the reaction mixture was poured into 40 mL of water and extracted with diethyl ether (200 mL total volume). The combined organic phases were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 651 mg (99% yield) of the title compound as a pale yellow oil which was used without further purification.

1. extractionextracted with diethyl ether (200 mL total volume)
2. washThe combined organic phases were washed with water, brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD 기록

ord-1cb6a45988d6443d80abc87aea48340c

출처 데이터셋

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08741897B2