Ethyl 2-(oxan-4-ylidene)acetate → Ethyl tetrahydropyran-4-ylacetate

HRID 1515754Notes

Reaction equation

HRID 1515754 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]=[C:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[CH3:2].[H][H]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 11105795Ethyl 2-(oxan-4-ylidene)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 2773412Ethyl tetrahydropyran-4-ylacetateYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (tetrahydro-pyran-4-ylidene)-acetic acid ethyl ester (27 g, 159 mmol) and 10% palladium on activated carbon (3 g) in methanol (300 mL) was stirred at 25° C. under 30 psi of hydrogen for 20 h. The catalyst was filtered off, washed with ethyl acetate and concentrated in vacuo to afford (tetrahydro-pyran-4-yl)-acetic acid ethyl ester (25 g, 91%) as a colorless oil which was used in the next step without purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efd2a38b30ed46058614bd4a4e5d6e27
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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