2-Propenoic acid, 3-(tetrahydro-2H-thiopyran-4-yl)-, ethyl ester → HCID 20143673, compound

HRID 280988Notes

Reaction equation

HRID 280988 reaction equation
[S: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]>[S: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 537977722-Propenoic acid, 3-(tetrahydro-2H-thiopyran-4-yl)-, ethyl ester

Product 1

HCID 20143673HCID 20143673, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(4-thianyl)acrylate (10 g) in ethanol (150 ml) is hydrogenated over 10% palladium-carbon (9 g, 50% wet) under atmospheric pressure. After the mixture is stirred for 20 minutes at room temperature and then for 8 hours at 50° C., the catalyst is removed by filtration. To the filtrate 10% palladium carbon (9 g, 50% wet) is added and the mixture is hydrogenated at 50° C. for 1 day. After the catalyst is removed by filtration, the filtrate is evaporated in vacuo to give ethyl 3-(4-thianyl)propionate (9.1 g) as an oil.

Workup

  1. waitfor 8 hours at 50° C.
  2. customthe catalyst is removed by filtration
  3. additionTo the filtrate 10% palladium carbon (9 g, 50% wet) is added
  4. waitthe mixture is hydrogenated at 50° C. for 1 day
  5. customAfter the catalyst is removed by filtration
  6. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-b52d3dec878d4576bc2b6b941d45033c
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

Loading…