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

HRID 980616Notes

Reaction equation

HRID 980616 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

In 200 ml of ethanol is dissolved 17 g of ethyl 3-(3,4,5,6-tetrahydro-2H-pyran -4-yl)acrylate, and a catalytic reduction reaction is carried out at ordinary temperature and at atmospheric pressure using 4 g of 10% palladium-carbon (50% in water) as a catalyst. After absorption of hydrogen stops, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is distilled under vacuum to give 15 g (bp 121-123°/16 mmHg)of ethyl 3-(3,4,5,6-tetrahydro-2H-pyran -4-yl)propionate as an oily material.

Workup

  1. customa catalytic reduction reaction
  2. customAfter absorption of hydrogen
  3. customthe catalyst is removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-24f2ac3b90234c8f94a445112b01fe35
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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