Potassium Hydroxide → HCID 22102325, compound

HRID 326722Notes

Reaction equation

HRID 326722 reaction equation
[C:1]([C:6]([CH3:22])([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])([O:3][CH2:4][CH3:5])=[O:2].[OH-].[K+]>C(O)C>[C:1]([C:6]([CH3:22])([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:7]([OH:9])=[O:8])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12724509HCID 12724509, compound

Product 1

HCID 22102325HCID 22102325, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-carboethoxy-3-(3-indolyl)-2-methylpropionate (1.8 g, 5.95 mmol) (S. Masanori, et al., Heterocycles, 1981, 16:941-9), was added to a solution of potassium hydroxide (380 mg, 5.76 mmol) in 4 mL of ethanol. The reaction mixture was stirred at ambient temperature overnight and then heated on a steam bath for 2 hours. The ethanol was evaporated and water (20 mL) was added. The aqueous mixture was extracted with diethyl ether (3×20 mL). The pH of the aqueous layer was adjusted to approximately 1 and it was then extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.5 g (92% yield) of the title compound.

Workup

  1. temperatureheated on a steam bath for 2 hours
  2. customThe ethanol was evaporated
  3. additionwater (20 mL) was added
  4. extractionThe aqueous mixture was extracted with diethyl ether (3×20 mL)
  5. extractionwas then extracted with ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a9b39215ba74e57ae1cddeb9210f957
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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