Methane, dichloromethoxy- → 6-Methoxy-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde

HRID 1243995Notes

Reaction equation

HRID 1243995 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.[CH3:16][O:17]C(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][C:4]=1[CH:16]=[O:17]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 219318586-Methoxy-1,3,3-trimethylindolin-2-one

Product 1

HCID 219318736-Methoxy-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred ice-cold solution of 6-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (1.0 g, 4.87 mmol) in 30 mL of CH2Cl2 was added TiCl4 (4.80 mL, 43.8 mmol) followed by α,α-dichloromethyl methyl ether (1.98 mL, 21.9 mmol). The reaction was stirred overnight at room temperature and was then quenched with 20 mL of water. The aqueous layer was extracted with CH2Cl2 (2×20 mL) and the combined organic portions were washed successively with satd NaHCO3, brine and water, dried with Na2SO4, and concentrated. The crude product was recrystallized from isopropanol/isopropyl ether to give 680 mg (60%) of a white solid (mp 192–194° C.). A second crop afforded an additional 213 mg for a total yield of 78%.

Workup

  1. customwas then quenched with 20 mL of water
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  3. washthe combined organic portions were washed successively with satd NaHCO3, brine and water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from isopropanol/isopropyl ether

Sources & evidence

ORD record
ord-42a34f56ff834b54809721579009cb1a
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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