Hydrochloric Acid → Ethyl 5-(2-thienyl)pentanoate

HRID 2289426Notes

Reaction equation

HRID 2289426 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C1COCC1.Cl>[OH-].[Pd+2].[OH-].CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 54305005Ethyl 5-(thiophen-2-YL)penta-2,4-dienoate

Product 1

HCID 21712768Ethyl 5-(2-thienyl)pentanoateYield 76.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 5-(2-thienyl)-2,4-pentdienoate (20.20 g), 10% palladium hydroxide (Pd(OH)2) (2.04 g), THF (200 ml), MeOH (100 ml) and 1 N HCl (10 ml) was stirred at r.t. under nitrogen atmosphere for 3.5 hours. After removal of insoluble solids, the filtrate was evaporated in vacuo, and the residue was dissolved with a mixture of AcOEt and water. The organic layer was washed with saturated aqueous solution of NaHCO3, water and brine, and dried over MgSO4, and evaporated in vacuo to give ethyl 5-(2-thienyl)pentanoate (15.70 g).

Workup

  1. customAfter removal of insoluble solids
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionthe residue was dissolved with a mixture of AcOEt and water
  4. washThe organic layer was washed with saturated aqueous solution of NaHCO3, water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cffc4a68ec8d422792e60987b818d473
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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