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

HRID 649406Notes

Reaction equation

HRID 649406 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-9db5989423004334ad393ad4eeb3335f
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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