Ethanol → Ethyl 1-phenylindole-3-glyoxylate

HRID 863544

Reaction equation

HRID 863544 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](Cl)(=[O:20])[C:17](Cl)=[O:18].[CH2:22]([OH:24])[CH3:23]>C(OCC)C>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=[O:20])[C:17]([O:24][CH2:22][CH3:23])=[O:18])=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 1820291-Phenyl-1H-indole

Product 1

HCID 54522388Ethyl 1-phenylindole-3-glyoxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An ice-cooled solution of 10 g (51.8 mmol) of 1-phenylindole in 100 ml of anhydrous diethyl ether was treated dropwise during 5 minutes with a solution of 6 ml (68.8 mmol) of oxalyl chloride in 20 ml of anhydrous diethyl ether. The mixture was stirred for 3 hours while cooling with ice and then treated with 25 ml of ethanol in one portion. After stirring for 10 minutes, the solvent was removed under reduced pressure and the residual solid was crystallized from 60 ml of ethanol to give 12.38 g of ethyl 1-phenylindole-3-glyoxylate as a pale yellow solid of melting point 109°-110° C.

Workup

  1. temperaturewhile cooling with ice
  2. stirringAfter stirring for 10 minutes
  3. customthe solvent was removed under reduced pressure
  4. customthe residual solid was crystallized from 60 ml of ethanol

Sources & evidence

ORD record
ord-74de5377f25a4801900574f2bd9a1c83
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Linked notes

Loading…