ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoate → Ethyl 3-tetrahydro-2H-pyran-4-ylpropanoate

HRID 280987Notes

Reaction equation

HRID 280987 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][CH2:2]1>C(O)C.[C].[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 54040092ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoate

Product 1

HCID 20143676Ethyl 3-tetrahydro-2H-pyran-4-ylpropanoateYield 87.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(3,4,5,6-tetrahydro-2H-pyran-4-yl)acrylate (17 g) in ethanol (200 ml) is catalytically hydrogenated over 10% palladium-carbon (4 g, 50% wet) at room temperature under atmospheric pressure. After the absorption of hydrogen has ceased, the catalyst is removed by filtration and the filtrate is concentrated in vacuo. The oily residue is purified by vacuum distillation to give ethyl 3-(3,4,5,6-tetrahydro-2H-pyran-4-yl)propionate (15 g) as an oil.

Workup

  1. customAfter the absorption of hydrogen
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated in vacuo
  4. distillationThe oily residue is purified by vacuum distillation

Sources & evidence

ORD record
ord-9dc1e3945b9d48b8b997ce0ee58592b9
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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