Ammonium formate → Ethyl tetrahydropyran-4-ylacetate

HRID 516885Notes

Reaction equation

HRID 516885 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-])=O.[NH4+]>CO.[Pd].[C]>[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

5

Reactant 2

HCID 2723923Ammonium formateHCID 11105795Ethyl 2-(oxan-4-ylidene)acetate

Product 1

HCID 2773412Ethyl tetrahydropyran-4-ylacetateYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture composed of ethyl 2-(2H-pyran-4(3H,5H,6H)-ylidene)acetate (10 g, 58.75 mmol) and ammonium formate (37 g, 587.54 mmol) in methanol (150 ml) was added 10% Pd-carbon (1.0 g) at room temperature, and the mixture was stirred at 70° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, and the catalyst was collected by filtration through Celite pad and was washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6) to give the title compound as an oil (7.9 g, yield 78%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe catalyst was collected by filtration through Celite pad
  3. washwas washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6)

Sources & evidence

ORD record
ord-241aa52babaf476b90135eaebc54188a
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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