Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate → Ethyl tetrahydro-4-oxo-2H-pyran-2-carboxylate

HRID 1774168Notes

Reaction equation

HRID 1774168 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][C:10](=[O:12])[CH:9]=[CH:8][O:7]1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][C:10](=[O:12])[CH2:9][CH2:8][O:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 22495097Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate

Product 1

HCID 54067561Ethyl tetrahydro-4-oxo-2H-pyran-2-carboxylateYield 33.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester (8.0 g, 46 mmol) and Pd/C (10%, 0.20 g) in ethyl acetate (70 mL) was stirred under hydrogen (1 atm) for 4 hours. The mixture was filtered through a pad of Celite®. The filtrate was concentrated, and the residue was purified by silica gel column using 30% EtOAc in petroleum ether to give 4-oxo-tetrahydro-pyran-2-carboxylic acid ethyl ester (2.62 g, 33% yield) as an oil. 1H NMR (500 MHz, CDCl3) δ 4.40 (m, 1H), 4.23-4.31 (m, 3H), 3.79 (m, 1H), 2.61-2.74 (m, 3H), 2.40 (d, J=15.0 Hz, 1H), 1.31 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-04d5cd536511472a9aa1dab71b3171e4
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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