(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid ethyl ester → (1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid

HRID 1445911Notes

Reaction equation

HRID 1445911 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([CH3:23])[N:11]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C>C1COCC1.O.O.[OH-].[Li+]>[CH2:16]([N:11]1[C:12]2[C:8](=[C:7]([O:6][CH2:5][C:4]([OH:24])=[O:3])[CH:15]=[CH:14][CH:13]=2)[CH:9]=[C:10]1[CH3:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 59170327(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid ethyl ester

Product 1

HCID 18461534(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid

Reagents, catalysts & solvents 2

HCID 168937Lithium hydroxide, monohydrateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid ethyl ester (4) (0.80 g, 2.48 mmole) in THF:H2O (4:1, 10 mL), lithium hydroxide monohydrate was added (0.118 g, 4.96 mmole). The mixture was stirred at room temperature for 1 h. THF was evaporated and then crushed ice was added to the aqueous mixture; the resulting solid was collected by filtration to afford intermediate (5) as a solid. Yield: 0.67 g, 92% 1H NMR: 05-038-055

Workup

  1. customTHF was evaporated
  2. additioncrushed ice was added to the aqueous mixture
  3. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-28c99ca43e664b2da6c75e8871ff1854
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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