Potassium Hydroxide → HCID 21460005, compound

HRID 1941129Notes

Reaction equation

HRID 1941129 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:27])=[C:5]([CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([O:23]C)=[O:22])[C:6]=1[CH2:7][CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH3:1][C:2]1[S:3][C:4]([CH3:27])=[C:5]([CH2:17][CH2:18][C:19]([CH3:25])([CH3:26])[CH2:20][C:21]([OH:23])=[O:22])[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21459987HCID 21459987, compound

Product 1

HCID 21460005HCID 21460005, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
210 °C

Procedure

6.4 g (0.0166 mol) of 2,5-dimethyl-3-(3-oxo-3-phenylpropyl)-4-(4-methoxycarbonyl-3,3-dimethylbutyl)thiophene and 100 ml of triethylene glycol are placed in a 250 ml three-necked flask fitted with a mechanical stirrer, a condenser and a thermometer. The temperature is brought to 60° C., 1.86 g (0.0580 mol) of 80% hydrazine hydrate are added to the reaction mixture and then, at 90° C., 2.84 g (0.050 mol) of potassium hydroxide are added. The reaction mixture is then brought to a vigorous reflux and, after the removal of water by distillation, the temperature is maintained at 210° C. for 45 minutes. After cooling, the mixture is hydrolysed with a mixture of water/ice/concentrated HCl (200 g/100 g/17 ml) and then extracted with ether. The combined organic phases are washed with dilute HCl, H2O, and then dried over MgSO4, rendered colourless with carbon black and concentrated to yield 4.5 g of 2,5-dimethyl-3-(3-phenylpropyl)-4-(4-carboxy-3,3-dimethylbutyl)thiophene in the form of a pale yellow oil, yield: 75%.

Workup

  1. customfitted with a mechanical stirrer, a condenser
  2. customis brought to 60° C.
  3. temperaturea vigorous reflux
  4. customafter the removal of water
  5. distillationby distillation
  6. temperatureAfter cooling
  7. additionthe mixture is hydrolysed with a mixture of water/ice/concentrated HCl (200 g/100 g/17 ml)
  8. extractionextracted with ether
  9. washThe combined organic phases are washed with dilute HCl, H2O
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-babaad9acc6c4b3398c0f3d88ba403aa
Source dataset
uspto-grants-1997_12
Patent number
US05703074

Reaction notes

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