Hydrochloric Acid → HCID 23510171, compound

HRID 1883159Notes

Reaction equation

HRID 1883159 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=[O:11].[OH-].[K+].[CH3:17][C:18]1([O:21][CH2:20]1)[CH3:19].Cl>CS(C)=O.C(OCC)(=O)C.O>[OH:21][C:18]([CH3:20])([CH3:19])[CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11208Isobutylene oxideHCID 14797Potassium HydroxideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 23510171HCID 23510171, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 760 mg of ethyl 2-indole carboxylate (4 mmol) dissolved in 8 ml dimethyl sulfoxide was added 290 mg of crushed potassium hydroxide (4.4 mmol). The mixture was stirred for approximately 30 minutes. 1.8 ml of isobutylene oxide was then added and the mixture was stirred at 50 C for 65 hours. The reaction was worked up by addition of water, 1M HCl to adjust the pH to 4-5, and ethyl acetate. The layers were separated and the ethyl acetate layer was washed with brine and dried over sodium sulfate. Evaporation gave 1-(2-hydroxy-2-methyl-propyl)-1H-indole-2-carboxylic acid (840 mg) as a solid (M−H=233) that was used directly in the next step.

Workup

  1. stirringthe mixture was stirred at 50 C for 65 hours
  2. customThe layers were separated
  3. washthe ethyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-ba466cebb95c45e384af90d6eb6be7d8
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

Loading…