Methanol → 3-Phenylcycloheptan-1-one

Temperatur

50 °C

Next, the scope of boronic acids that can be utilized was briefly examined. More specifically, the general experimental procedure for the 1,4-addition of arylboronic acids to enones will be described using 2-cyclohexen-1-one and phenylboronic acid. A mixture of 2-cyclohexen-1-one (96 mg, 1 mmol) and phenylboronic acid (158 mg, 1.3 mmol) was taken in a round bottom flask. A toluene solution (3 ml) containing Rh(acac)(CO)2 (5 mg, 0.02 mmol) and JanaPhos (70 mg, 0.03 mmol, Rh/P=1/3) was added to it in an inert atmosphere. A solution of methanol and water (1:1, 0.5 ml) was added to it via syringe. The reaction mixture was heated at 50° C. for 15 hours until the starting material was consumed as indicated by TLC. Then 25 ml methanol was added to it mixture and the catalyst was precipitated out as a white solid. It was filtered out by a Schlenk filter and underwent for the consecutive runs. The filtrate was evaporated under reduced pressure to obtain the crude product which was further purified by column chromatography (10% ethyl acetate in hexane) to obtain the pure product (144 mg, 83% yield).

1. customwas taken in a round bottom flask
2. additionwas added to it in an inert atmosphere
3. customwas consumed
4. additionThen 25 ml methanol was added to it mixture
5. customthe catalyst was precipitated out as a white solid
6. filtrationIt was filtered out by a Schlenk
7. filtrationfilter
8. customThe filtrate was evaporated under reduced pressure
9. customto obtain the crude product which
10. customwas further purified by column chromatography (10% ethyl acetate in hexane)

ORD-Eintrag

ord-8133ff6ab0a4471c84db08d566b5e465

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08921486B2