Water → 5-(2-Thienyl)valeric acid

HRID 650590Notes

Reaction equation

HRID 650590 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[Na+].O.O1CCCC1>C(OCC)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21712768Ethyl 5-(2-thienyl)pentanoate

Product 1

HCID 1523245-(2-Thienyl)valeric acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 5-(2-thienyl)pentanoate (15.40 g), sodium hydroxide (NaOH) (2.90 g), water (H2O) (18 ml), and tetrahydrofuran (THF) (100 ml) was stirred at reflux for 2.5 hours. The reaction mixture was poured into a mixture of water and diethyl ether (Et2O). The aqueous layer was separated, and acidified with 6 N hydrochloric acid (HCl), and extracted with ethyl acetate (AcOEt). The organic layer was washed with water and brine, and dried over magnesium sulfate (MgSO4), and evaporated to give 5-(2-thienyl)pentanoic acid (12.07 g) as an oil.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (AcOEt)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-91252d11a028438b8c34d158cae6bdd7
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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