3-Heptanone → HCID 68512433, compound

To a solution of ethyl 5-bromo-2-ethylthiophene-3-carboxylate (3.00 g) synthesized in Example 69 (4) in tetrahydrofuran (50 mL) was added dropwise 1.0M isopropylmagnesium bromide-tetrahydrofuran solution (13.7 mL) at −45° C. After stirring under an argon atmosphere for 1 hr, 1.0M isopropylmagnesium bromide-tetrahydrofuran solution (13.7 mL) was added dropwise, and the mixture was stirred for 1 hr. 3-Heptanone (6.04 mL) was added dropwise, and the mixture was stirred at −45° C. for 1 hr, and at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title compound (3.06 g, quantitative) as a colorless oil.

1. stirringthe mixture was stirred for 1 hr
2. stirringthe mixture was stirred at −45° C. for 1 hr
3. waitat room temperature for 1 hr
4. customto quench
5. customthe reaction
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

ORD record

ord-888730f20d674d77a67762f5c23b3b4f

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2