Sodium Hydroxide → HCID 67273211, compound

HRID 1020918Notes

Reaction equation

HRID 1020918 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:23]2[CH2:27][CH2:26][CH2:25][CH:24]=2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[C:23]1([C:11]2[NH:10][C:18]3[C:13]([CH:12]=2)=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67273154HCID 67273154, compound

Product 1

HCID 67273211HCID 67273211, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 291 mg (0.76 mmol) of the phenylsulfonamide intermediate from step 3 in 50 mL EtOH was added 5 mL 10% NaOH solution. The reaction was heated to reflux overnight and then concentrated. The residue was dissolved in EtOAc, washed with 2N Na2CO3 solution, H2O, aqueous NaCl solution, dried (MgSO4), and concentrated under vacuum to yield 180 mg of 2-cyclopent-1-enyl-4,5-dimethoxy-1H-indole (97%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 2N Na2CO3 solution, H2O, aqueous NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-db94dbbd12de40a491c48efc13c09c28
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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