Diethyl Ether → HCID 53415958, compound

HRID 1009545Notes

Reaction equation

HRID 1009545 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH:14]=[O:15])=[CH:4]1)[CH3:2].[O-:16][Mn](=O)(=O)=O.[K+].CCOCC>CC(C)=O.O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]([OH:16])=[O:15])=[CH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 516875Potassium Permanganate2×HCID 45094683HCID 45094683, compound

Product 1

HCID 53415958HCID 53415958, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

1-Ethyl-6-methoxy-1H-indole-3-carbaldehyde (600 mg, 2.95 mmol) is dissolved in acetone (85 mL). A solution of KMnO4 (450 mg, 2.85 mmol) in H2O (28 mL) is added. This is stirred at room temperature for 5 hours. Another solution of KMnO4 (450 mg, 2.85 mmol) in H2O (25 mL) is then added. After stirring for another hour at room temperature, the reaction is complete. The reaction mixture is quenched with 10% H2O2 (1.5 mL), and is then filtered through celite. The filtrate is stripped down under vacuum to roughly 1/3 of the volume. The residue is acidified with 6N HCl, and is extracted into ethyl acetate. Purification by silica gel column (hexanes/acetone/acetic acid, 70/30/1) yields crude product. Trituration with ether yields pure 1-ethyl-6-methoxy-1H-indole-3-carboxylic acid (365 mg, 56%) as a yellow solid.

Workup

  1. stirringAfter stirring for another hour at room temperature
  2. customThe reaction mixture is quenched with 10% H2O2 (1.5 mL)
  3. filtrationis then filtered through celite
  4. extractionis extracted into ethyl acetate
  5. customPurification by silica gel column (hexanes/acetone/acetic acid, 70/30/1)
  6. customyields crude product

Sources & evidence

ORD record
ord-be214c04995b424f9917c7152829e276
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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