Methyl chloroglyoxylate → HCID 59379802, compound

HRID 598707Notes

Reaction equation

HRID 598707 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:11])[C:8](Cl)=[O:9].[C:12]1([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:11])[C:8]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:13][CH:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 2848155HCID 2848155, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59379802HCID 59379802, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added CH2Cl2 (100 mL) followed by the addition of AlCl3 (2.2 g, 16.3 mmol). The suspension was stirred 5 min at room temperature, methylchloroglyoxylate (1.66 mL, 17.88 mmol) was added and stirred an additional 5 min, followed by the addition of 11 (0.841 g, 3.27 mmol). The mixture was stirred at room temperature overnight, quenched with water, neutralized with NaHCO3 and extracted with EtOAc three times. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent removed leaving a brown oil. The material was purified by column chromatography (0-5% MeOH/CH2Cl2) providing 1.08 g of 12 (97%) as a yellow solid. LC-MS: Calculated mass=343. Observed mass=344.

Workup

  1. stirringstirred an additional 5 min
  2. stirringThe mixture was stirred at room temperature overnight
  3. customquenched with water
  4. extractionextracted with EtOAc three times
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customleaving a brown oil
  10. customThe material was purified by column chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9280559408c54518a547e991e8ca9675
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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