Lithium Hydroxide → HCID 54353537, compound

HRID 1066799Notes

Reaction equation

HRID 1066799 reaction equation
Cl[C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[O:4][CH2:5][C:6]1[N:7]([CH3:22])[C:8]2[C:13]([C:14]=1[CH:15](O)[CH2:16][C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=[CH:10][CH:9]=2.[OH-].[Li+]>O1CCCC1>[Cl:27][C:25]1[CH:24]=[CH:23][C:3]([O:4][CH2:5][C:6]2[N:7]([CH3:22])[C:8]3[C:13]([C:14]=2[CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:2][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21195962HCID 21195962, compound

Product 1

HCID 54353537HCID 54353537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a round bottom flask is charged with 2-[(2,4-dichlorophenoxy)methyl]-1-methyl-3-[1-hydroxy-2-(methoxycarbonyl)ethyl]-1H-indole (Example 55) (0.149 g, 0.398 mmol) and 6.11 ml of dry tetrahydrofuran. To this solution is added 1.22 ml of a 2.0 N lithium hydroxide aqueous solution and the resulting mixture was stirred at room temperature for about two hours. The solvents were removed in vacuo and the residue is partitioned between methylene chloride and water. The aqueous fraction was extracted twice with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The desired title product was triturated with diethyl ether.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue is partitioned between methylene chloride and water
  3. extractionThe aqueous fraction was extracted twice with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customThe desired title product was triturated with diethyl ether

Sources & evidence

ORD record
ord-16a1c4bbfc7e479889f36634035b2cd9
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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