Potassium Hydroxide → HCID 21271270, compound

HRID 1194009Notes

Reaction equation

HRID 1194009 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([C:20]([O:22]C)=[O:21])[S:18][CH:19]=2)[O:4][N:3]=1.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([C:20]([OH:22])=[O:21])[S:18][CH:19]=2)[O:4][N:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21271267HCID 21271267, compound

Product 1

HCID 21271270HCID 21271270, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

11.34 g (33.61 mmol) of methyl 4-(7-(3-methyl-5-isoxazolyl)-heptyloxy)-2-thiophenecarboxylate are heated under reflux in 95 ml of ethanol and 45 ml of water, and 2.18 g (38.9 mmol) of KOH, dissolved in 70 ml of water and 46 ml of ethanol, are added dropwise to this solution. After the mixture has been heated under reflux for 3 hours, it is cooled and concentrated, the residue is partitioned between water and ether and the aqueous phase, after acidification to pH 1 with 2N HCl, is extracted several times with ether. The combined organic phases are dried over sodium sulfate/active charcoal and evaporated.

Workup

  1. temperatureAfter the mixture has been heated
  2. temperatureunder reflux for 3 hours
  3. temperatureit is cooled
  4. concentrationconcentrated
  5. customthe residue is partitioned between water and ether
  6. extractionthe aqueous phase, after acidification to pH 1 with 2N HCl, is extracted several times with ether
  7. dry with materialThe combined organic phases are dried over sodium sulfate/active charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-ed80fbe2a5644b618cbcb013373728d4
Source dataset
uspto-grants-1989_03
Patent number
US04812472

Reaction notes

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