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

HRID 1350119Notes

Reaction equation

HRID 1350119 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1>C(O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 11105795Ethyl 2-(oxan-4-ylidene)acetate

Product 1

HCID 2773412Ethyl tetrahydropyran-4-ylacetateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-oxanylidene)acetate (22.0 g, 139 mmol) in ethanol (50 mL) was added 10% Pd/C (2.2 g) and the mixture subjected to hydrogenation overnight on a Parr apparatus (50 psi). The catalyst was removed by filtration through Celite, which was washed with ethanol (25 mL). Removal of solvent from the combined filtrates by rotary evaporation gave the desired product as a colorless oil (22.0 g, 98.5%).

Workup

  1. customThe catalyst was removed by filtration through Celite, which
  2. washwas washed with ethanol (25 mL)
  3. customRemoval of solvent from the combined filtrates
  4. customby rotary evaporation

Sources & evidence

ORD record
ord-31befb73fc5542668f94981a056a6592
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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