Phenylacetylene → HCID 22990210, compound

Temperature

80 °C

A mixture of ethynylbenzene (511 mg, 5.00 mmol), methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylate (708 mg, 2.50 mmol), dichlorobis(triphenylphosphine)palladium (176 mg, 0.25 mmol), copper iodide (48 mg, 0.25 mmol) and triethylamine (15 ml) was stirred at 80° C. for 17 hours. The reaction mixture was concentrated under reduced pressure and was mixed with ethyl acetate (70 ml), and the resulting mixture was washed successively with 1 N hydrochloric acid (5 ml×3) and an aqueous saturated solution of sodium chloride (5 ml). The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 35 g, ethyl acetate/hexane=1/19). The objective fractions were concentrated under reduced pressure and were mixed with diisopropyl ether, and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain methyl 7-phenylethynyl-2,3-dihydro-1-benzooxepine-4-carboxylate (525 mg, 1.73 mmol, 69%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionwas mixed with ethyl acetate (70 ml)
3. washthe resulting mixture was washed successively with 1 N hydrochloric acid (5 ml×3)
4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
5. concentrationwas then concentrated under reduced pressure
6. concentrationThe objective fractions were concentrated under reduced pressure
7. additionwere mixed with diisopropyl ether
8. filtrationan insoluble material was collected by filtration
9. washThe insoluble material was washed with diisopropyl ether
10. customwas then dried under reduced pressure

ORD record

ord-c30d002f83934c1d92b63c2274352d33

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627651B1