Potassium Hydroxide → HCID 54191578, compound

HRID 1105557Notes

Reaction equation

HRID 1105557 reaction equation
C([O:7][C:8](=[O:24])[CH2:9][C:10]1[S:11][C:12]([CH:15]=[CH:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:14]=1)CCCCC.[OH-].[K+]>C(O)C.O>[O:23]=[C:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:16]=[CH:15][C:12]1[S:11][C:10]([CH2:9][C:8]([OH:24])=[O:7])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54378847HCID 54378847, compound

Product 1

HCID 54191578HCID 54191578, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

3.5 G of 2-[5-(3-oxooct-1-enyl)thien-2-yl]acetic acid hexyl ester was dissolved in 20 ml of ethanol; then, a solution of 0.6 g of potassium hydroxide in 10 ml ethanol was added portionwise over aperiod of 4 hours. The resultant solution was stirred for an additional 4 hours, then was diluted with water. The water solution was extracted several times with ether, and the ether phases were discarded. The water solution was adjusted to pH 5.5 to 6 with dilute hydrochloric acid and extracted with ether, and the ether phase was washed with water, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by column chromatography (silica gel, using benzene and ethyl acetate as eluants). There were thus obtained 1.2 g (45% yield) of the desired product, melting at 51° C.

Workup

  1. extractionThe water solution was extracted several times with ether
  2. extractionextracted with ether
  3. washthe ether phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (silica gel, using benzene and ethyl acetate as eluants)

Sources & evidence

ORD record
ord-232f99d4eb194b2cb285b57be267d7e5
Source dataset
uspto-grants-1982_01
Patent number
US04309407

Reaction notes

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