Ethanol → HCID 21272043, compound

HRID 1193486Notes

Reaction equation

HRID 1193486 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C.[CH2:26]([OH:28])[CH3:27]>CCOCC>[C:20]1([CH2:19][O:18][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[NH:10][CH:9]=[C:17]3[C:1](=[O:5])[C:2]([O:28][CH2:26][CH3:27])=[O:3])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 54540393HCID 54540393, compound

Product 1

HCID 21272043HCID 21272043, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Oxalyl chloride (3.2 g, 2.2 mL, 24.7 mmol) was added dropwise under nitrogen to an ice cold solution of ethyl 7-(phenylmethoxy)-indole (2.3 g, 10.3 mmol) in anhydrous ether (40 mL). The mixture was stirred for 1 hour at room temperature during which time a yellow precipitate was formed. The solvent and the excess of oxalyl chloride was removed at reduced pressure to yield 7-(phenylmethoxy)-indol-3-yl-glyoxyl chloride. Ethanol (50 mL) was then added to the residue and the solution was stirred overnight under nitrogen at room temperature. Removal of the solvent in vacuo provided ethyl 7-(phenylmethoxy)-indol-3-yl-glyoxylate as a tan solid (3 g, 94%).

Workup

  1. customwas formed
  2. customThe solvent and the excess of oxalyl chloride was removed at reduced pressure
  3. customto yield 7-(phenylmethoxy)-indol-3-yl-glyoxyl chloride
  4. stirringthe solution was stirred overnight under nitrogen at room temperature
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-80bc4b64268849269feb2c47b02fcd26
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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