ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate

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ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate Basic information
Product Name:ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate
Synonyms:2H-Pyran-2-carboxylic acid, tetrahydro-4-oxo-, ethyl ester;ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate;ethyl 4-oxooxane-2-carboxylate;4-Oxotetrahydro-2H-pyran-2-carboxylic acid ethyl ester;Ethyl 4-Oxotetrahydropyran-2-carboxylate;4-Oxo-tetrahydro-pyran-2-carboxylic acid ethyl ester
CAS:287193-07-1
MF:C8H12O4
MW:172.18
EINECS:
Product Categories:
Mol File:287193-07-1.mol
ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate Structure
ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate Chemical Properties
Boiling point 84 °C(Press: 0.04 Torr)
density 1.162±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
AppearanceColorless to light yellow Liquid
Safety Information
HS Code 2932990090
MSDS Information
ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate Usage And Synthesis
UsesETHYL 4-OXOTETRAHYDRO-2H-PYRAN-2-CARBOXYLATE (cas# 287193-07-1) is a useful research chemical. It is used in the preparation of aminoquinazoline derivatives for use as A2a antagonists.
Synthesis
Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate

287193-06-0

ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate

287193-07-1

Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate (2.0 g, 11.75 mmol, 1.00 eq.) was dissolved in ethyl acetate (50 mL) in a 100 mL round-bottom flask under nitrogen atmosphere. 10% palladium/activated carbon (200 mg) was subsequently added. The system was degassed by three evacuation-nitrogen filling cycles. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the solid catalyst was removed by filtration and the filter cake was washed with ethyl acetate (3×). The combined filtrates were concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as eluent to afford ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate (1.62 g, 80% yield) as a light yellow oil.

References[1] Patent: WO2013/106535, 2013, A1. Location in patent: Paragraph 001250
[2] Patent: EP1214325, 2005, B1. Location in patent: Page/Page column 49-50
[3] Patent: US7019026, 2006, B1. Location in patent: Page/Page column 72
[4] Patent: US7115624, 2006, B1. Location in patent: Page/Page column 85-87
[5] Patent: WO2013/130976, 2013, A1. Location in patent: Paragraph 00288
ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate Preparation Products And Raw materials
Raw materialsEthyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate-->Activated carbon-->Ethyl acetate-->Hydrogen-->Palladium
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