Indole → Ethyl 3-indolylglyoxylate

HRID 1095346Notes

Reaction equation

HRID 1095346 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.) 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-e538b1bf3a20418aa517a7cf341d7ab0
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

Loading…