Potassium Hydroxide → 4-(2-Thienyl)Butyric Acid

HRID 874986Notes

Reaction equation

HRID 874986 reaction equation
O.NN.[OH-].[K+].O=[C:7]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH2:8][CH2:9][C:10]([OH:12])=[O:11]>C(O)CO.O>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 783853-(2-Thenoyl)propionic acid

Product 1

HCID 783864-(2-Thienyl)Butyric AcidYield 85%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Hydrazine hydrate (99%) (2.2 MI, 45.9 mmol) and KOH pellets (2.37 g, 42.4 mmol) were added to a solution of 4-oxo-4-(thiophen-2-yl)butanoic acid (2.3 g, 12.48 mmol) in ethylene glycol (30 MI), and the reaction mixture was heated to 180° C. for 10 h. The reaction mixture was cooled to room temperature and diluted with water. The aqueous layer was washed with diethyl ether, acidified with 6N HCl and then extracted with diethyl ether. The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 2% MeOH in CH2Cl2), to get 4-(thiophen-2-yl)butanoic acid (1.8 g, yield 85%). 1H NMR (300 MHz, DMSO-d6) δ 12.06 (s, 1H), 7.31-7.29 (m, 1H), 6.94-6.91 (m, 1H), 6.84-6.82 (m, 1H), 2.82-2.77 (t, J=7.7 Hz, 2H), 2.27-2.22 (t, J=7.3 Hz, 2H), 1.86-1.76 (m, 2H). MS (ESI) m/z: Calculated for C8H10O2S: 170.04. found: 170.8 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe aqueous layer was washed with diethyl ether
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e5df0e6292c248e185182b6eb16a1ee3
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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