Methanol → HCID 21950015, compound

HRID 2215815Notes

Reaction equation

HRID 2215815 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13].C(Cl)Cl.[CH3:20][O-:21].[Na+].CO>C(OCC)C>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:15])[C:12]([O:21][CH3:20])=[O:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 1379281H-Indole, 6-methyl-HCID 10942334Sodium Methoxide

Product 1

HCID 21950015HCID 21950015, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-methylindole (1.00 g, 7.62 mmol) in diethyl ether (10 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (4.0 mL, 8.0 mmol). The resulting solution was allowed to warm to room temperature. After 90 min, the solution was cooled to −78° C. To this solution was added 25% (w/w) solution of sodium methoxide in methanol (3.65 mL, 16.0 mmol). The resulting solution was allowed to warm to room temperature. After 1 h, the solution was filtered to give the title compound (894 mg, 54%) as a beige solid.

Workup

  1. temperaturethe solution was cooled to −78° C
  2. temperatureto warm to room temperature
  3. waitAfter 1 h
  4. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-fa73c128ecd84257ad971ead24b942a6
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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