Tetrahydrofuran → HCID 59389327, compound

A 2.71 mol/L n-butyl lithium-hexane solution (0.52 mL) was added dropwise to a solution of methyltriphenylphosphonium bromide (499 mg) in THE (5 mL) at 0° C. The mixture was stirred at room temperature for 30 min. The compound of Example 237 (80.0 mg) in THF (5 mL) was then added dropwise at 0° C. and the mixture was further stirred at room temperature for 2 hours. Subsequently, the reaction was quenched by adding a saturated aqueous solution of ammonium chloride and the reaction mixture was extracted with ethyl acetate (50 mL). The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate. The dried extract was concentrated and purification by silica gel column chromatography (hexane:ethyl acetate=1:2) and recrystallization (ethyl acetate-hexane) afforded the title compound as a pale yellow powder (7.1 mg).

1. stirringthe mixture was further stirred at room temperature for 2 hours
2. customSubsequently, the reaction was quenched
3. additionby adding a saturated aqueous solution of ammonium chloride
4. extractionthe reaction mixture was extracted with ethyl acetate (50 mL)
5. washThe extract was washed with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. extractionThe dried extract
8. concentrationwas concentrated
9. custompurification
10. customby silica gel column chromatography (hexane:ethyl acetate=1:2) and recrystallization (ethyl acetate-hexane)

ORD record

ord-772d243bab3a4e6bb2dc8e854ec74ca6

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763617B2