Tetrahydrofuran → 1-[4-Methoxy-3-(4-methoxybutyl)phenyl]ethanone

Temperatur

80 °C

To a solution of 4-bromo-1-methoxy-2-(4-methoxybutyl)benzene (523 mg) in tetrahydrofuran (10 mL) were added lithium chloride (326 mg), tetrakis(triphenylphosphine)palladium (0) (381 mg) and tri-n-butyltin-1-ethoxyvinyl 91.11 mL), and the mixture was heated to stir at 80° C. for 20 hours. The reaction solution was cooled to room temperature, and then thereto was added aqueous potassium fluoride solution, and the mixture was stirred for 30 minutes. The mixture was extracted with diethyl ether, and then thereto was added 10% hydrochloric acid, and the mixture was stirred for 1 hour. The organic layer was separated, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1) to give 1-[4-methoxy-3-(4-methoxybutyl)phenyl]ethanone [REx(24-1)] (195 mg) as a yellow oil.

1. temperaturewas heated
2. temperatureThe reaction solution was cooled to room temperature
3. stirringthe mixture was stirred for 30 minutes
4. extractionThe mixture was extracted with diethyl ether
5. additionwas added 10% hydrochloric acid
6. stirringthe mixture was stirred for 1 hour
7. customThe organic layer was separated
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1)

ORD-Eintrag

ord-ec3db68129f646a68435292c7338880d

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09278944B2