Methanol → HCID 117779067, compound

HRID 1526994Notes

Reaction equation

HRID 1526994 reaction equation
CO.[CH:3]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18]C)=[O:17])=[C:8]1[CH3:20])([CH2:5][CH3:6])[CH3:4].[OH-].[Li+]>O>[CH:3]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[C:8]1[CH3:20])([CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 117778811HCID 117778811, compound

Product 1

HCID 117779067HCID 117779067, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of methanol (10 mL) and water (2 mL), methyl 1-sec-butyl-2-methyl-1H-indole-3-carboxylate (141 mg, 0.58 mmol) and lithium hydroxide (100 mg, 2.4 mmol) were added. The mixture was stirred at room temperature for 12 hours. Then the reaction mixture was acidified by hydrochloric (1 M) to adjust pH=6 and extracted with dichloromethane (10 mL×3). The organic layers were combined and concentrated to give 1-sec-butyl-2-methyl-1H-indole-3-carboxylic acid (97 mg, 72%).

Workup

  1. extractionextracted with dichloromethane (10 mL×3)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d192889ce2004f4ab816057573b3af46
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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