Ethyl Acetate → Ethyl-3-oxo-5-phenylpent-4-enoate

Trans-cinnamic acid (5 mmol, manufactured by Fluka), 1,1′-carbonyl diimidazole (892 mg, 5.5 mmol, manufactured by Aldrich) and tetrahydrofuran (10 mL) were charged in a 25 mL round-bottom flask, followed by stirring at room temperature for 1 hour. 1M lithium bis(trimethylsilyl)amide (10 mL, 10 mmol, manufactured by Aldrich), ethyl acetate (977 μL, 10 mmol), and tetrahydrofuran (10 mL) were added to thereto, followed by stirring at −78° C. for 1 hour. Two solutions were mixed, gradually warmed and stirred at room temperature for 1 hour. A saturated ammonium chloride aqueous solution (50 mL) and ethyl acetate (50 mL) were added thereto, followed by separation of layers into two layers and washing with distilled water and saline. The organic layer was dried over anhydrous sodium sulfate and separated by column chromatography (n-Hex/EtOAc=15/1 (v/v)) to afford Compound 8a.

1. stirringby stirring at −78° C. for 1 hour
2. additionTwo solutions were mixed
3. temperaturegradually warmed
4. stirringstirred at room temperature for 1 hour
5. customfollowed by separation of layers into two layers
6. washwashing with distilled water and saline
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. customseparated by column chromatography (n-Hex/EtOAc=15/1 (v/v))

ORD record

ord-63a8dc5c60cf45ba8f8ce65ff454c2f0

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637674B2