Potassium Hydroxide → HCID 13409287, compound

HRID 1980541Notes

Reaction equation

HRID 1980541 reaction equation
[OH-].[K+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]C)=[O:20])[CH2:15][CH:14]=2)=[C:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH:14]=2)=[C:5]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13409286HCID 13409286, compound

Product 1

HCID 13409287HCID 13409287, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.6 g (0.085 mol) of potassium hydroxide in 150 mL of ethanol was added 6.9 g (0.020 mol) of methyl 4-(1-methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate (Example 5). This mixture was heated under reflux until solution resulted. Heating was continued 4 h, then the solution was cooled, concentrated in vacuo, dissolved in water, and made acidic with 2N hydrochloric acid to give a precipitate. The solid was collected, washed with water, dissolved in ether, washed with water, dried over sodium sulfate, charcoaled, concentrated in vacuo, and recrystallized twice from ether:hexane to give 5.6 g (85%) of 4-(1-methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid, m.p. 171°-172° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureunder reflux until solution
  3. customresulted
  4. temperatureHeating
  5. temperaturethe solution was cooled
  6. concentrationconcentrated in vacuo
  7. dissolutiondissolved in water
  8. customto give a precipitate
  9. customThe solid was collected
  10. washwashed with water
  11. dissolutiondissolved in ether
  12. washwashed with water
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated in vacuo
  15. customrecrystallized twice from ether

Sources & evidence

ORD record
ord-9008362d5f5a4665bf432f2a6db12366
Source dataset
uspto-grants-1985_04
Patent number
US04510158

Reaction notes

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