Indole → Ethyl 3-indolylglyoxylate

HRID 1984506Notes

Reaction equation

HRID 1984506 reaction equation
N1C=CC=CC=1.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(OCC)C>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]1

Participants

5

Reactant 3

HCID 798IndoleHCID 1049PyridineHCID 20884Ethoxalyl chloride

Product 1

HCID 101242Ethyl 3-indolylglyoxylateYield 84.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridine (40 mL, 492 mmol) was added in a single portion to a chilled solution (0° C.) solution of indole (48 g, 410 mmol) in diethyl ether (820 mL). Ethyl chlorooxoacetate (50 mL, 451 mmol) was added dropwise. The resulting suspension was allowed to warm to ambient temperature over a period of 20 hours. The solid was isolated by filtration and washed with diethyl ether. The solid was combined with water (1 L), stirred for 1 hour, and then isolated by filtration to provide 75 g of ethyl (1H-indol-3-yl)(oxo)acetate.

Workup

  1. customThe solid was isolated by filtration
  2. washwashed with diethyl ether
  3. customisolated by filtration

Sources & evidence

ORD record
ord-711be8649cce4aacb5fe44530d80303f
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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