ChemicalBook CAS DataBase List 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one synthesis

13synthesis methods

Product Name:1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one
CAS Number:196597-78-1
Molecular formula:C11H10O2
Molecular Weight:174.2

4,5-Dibromo-1,2,6,7-tertahydro-8H-indeno[5,4-b]furan-8-one

196597-77-0
79 suppliers
$110.00/25mg

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

196597-78-1
258 suppliers
$31.00/250mg

Yield:196597-78-1 88.6%

Reaction Conditions:

with hydrogen;sodium acetate;palladium 10% on activated carbon in methanol at 40; under 2175.22 - 3675.37 Torr; for 8 h;

Steps:

1.1
4,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (280 kg, 843mol), anhydrous sodium acetate (173 kg, 2109 mol), methanol (6384 L) were mixed, and the reaction system was replaced with nitrogen. Then, to the reaction mixture was added 10% Pd/C (30.8 kg, as dry weight), and pressurized with hydrogen to 0.29 to 0.49 MPa, and catalytically reduced at about 40°C for 8 hrs with stirring at such a stirring rate that the gas-liquid overall mass transfer coefficient K_La(1/hr) is about 15. The catalyst was filtered, and the filtrate was concentrated under reduced pressure, and further water was added to the residue, followed by concentrating under reduced pressure to substitute the solvent, cooling and stirring for 1 hr to mature. The crystallization solution was filtered to give wet crystals of title compound (amount 127 kg as dry weight, yield 86.6%). The content of dimer in the wet crystals was less than 0.1% by weight.

References:

Takeda Pharmaceutical Company Limited EP1792899, 2007, A1 Location in patent:Page/Page column 13

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