Tetrahydrofuran → Ethyl 3-[2-[2-(5-cyanobenzo[b]thien-2-yl)ethyl]-4-ethoxy-5-methoxyphenyl]propionate

To a mixture solution of 50 ml of tetrahydrofuran and 50 ml of ethanol were dissolved 1.5 g of 5-cyanobenzo[b]thiophene-2-carbaldehyde and 6.34 g of crude [5-ethoxy-2-(2-ethoxycarbonylethyl)-4-methoxyphenyl]methyltriphenylphosphonium chloride obtained in the above step d). 1.83 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added thereto, followed by stirring at room temperature for 18 hours. The resulting reaction solution was concentrated under a reduced pressure, and the residue was dissolved in a mixture solution of 20 ml of tetrahydrofuran and 20 ml of ethanol. The thus prepared solution was mixed with 1.70 g of 10% palladium carbon catalyst (50% wet type) and subjected to catalytic hydrogenation under normal pressure until hydrogen absorption was completed. After removing the catalyst by filtration, the solvent was distilled off. By subjecting the resulting residue to silica gel column chromatography, 1.2 g of oily ethyl 3-[2-[2-(5-cyanobenzo[b]thien-2-yl)ethyl]-4-ethoxy-5-methoxyphenyl]propionate was obtained.

1. customobtained in the above step d)
2. customThe resulting reaction solution
3. concentrationwas concentrated under a reduced pressure
4. dissolutionthe residue was dissolved in a mixture solution of 20 ml of tetrahydrofuran and 20 ml of ethanol
5. additionThe thus prepared solution was mixed with 1.70 g of 10% palladium carbon catalyst (50% wet type)
6. customsubjected to catalytic hydrogenation under normal pressure until hydrogen absorption
7. customAfter removing the catalyst
8. filtrationby filtration
9. distillationthe solvent was distilled off

ORD-Eintrag

ord-bb12549ef2b04efa9ff976689bfe0e20

Quelldatensatz

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05962695