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

HRID 1594821Notes

Reaction equation

HRID 1594821 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].[H][H]>CCOC(C)=O.[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

5

Reactant 2

HCID 22495097Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylateHCID 178418361HCID 178418361, compound

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, 46.0 mmol) and Pd/C (10%, 0.20 g) in EtOAc (70 mL) was shaken in a Parr bottle with hydrogen at 50 psi overnight and filtered through a pad of Celite. The filtrate was concentrated and the residue was distilled to give 2.62 g (33%) of yellowish oil: 1H NMR (CDCl3) δ 1.29 (t, 3H), 2.40 (d, 1H), 2.58-2.75 (m 3H), 3.79 (tt, 1H), 4.23 (q, 2H), 4.28 (m 1H), 4.40 (m, 1H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. distillationthe residue was distilled

Sources & evidence

ORD record
ord-98730daf56ff4475a1c7d90c76137141
Source dataset
uspto-grants-2001_09
Patent number
US06284764B1

Reaction notes

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