Water → HCID 68460883, compound

Temperature

0 °C

Under a nitrogen stream, to 4-bromo-2-((4-ethylphenyl)methyl)thiophene (2.80 g, 10.0 mmol) in anhydrous THF (40 ml), LDA (2.0 M, 5.50 ml, 11.0 ml) was added dropwise at −78° C. over 5 minutes. After the reaction mixture was stirred at 0° C. for 30 minutes, a THF solution of ethylene oxide (10 ml) was added dropwise at −78° C. The reaction mixture was warmed to room temperature and stirred for 3 hours. After addition of water, the reaction mixture was extracted with ether. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:9)) to give the titled compound (2.55 g, 78%).

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred for 3 hours
3. extractionthe reaction mixture was extracted with ether
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated under reduced pressure
7. customto remove the solvent
8. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:9))

ORD record

ord-78d942227bea42ae9c05e11bffce5500

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767651B2