Water → HCID 68512194, compound

Temperature

-10 °C

A solution of 2-(thiophen-3-yl)-1,3-dioxolane (33.6 g) synthesized above in tetrahydrofuran (300 mL) was cooled to −10° C., 1.6M n-butyllithium in hexane solution (148 mL) was added dropwise, and the mixture was stirred for 1 hr under a nitrogen atmosphere. The reaction mixture was cooled to −78° C., methyl iodide (16.1 mL) was added, and the mixture was stirred at −78° C. for 30 min, and then at room temperature for 5 hr. Water was added to quench the reaction, the organic solvent was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give the title compound (26.0 g, 71%) as a yellow oil.

1. temperatureThe reaction mixture was cooled to −78° C.
2. stirringthe mixture was stirred at −78° C. for 30 min
3. waitat room temperature for 5 hr
4. customto quench
5. customthe reaction
6. customthe organic solvent was evaporated
7. customevaporator
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with saturated brine
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

ORD record

ord-56a561346b2d41a48b7bc9188cf30d61

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2