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

HRID 1244027Notes

Reaction equation

HRID 1244027 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>[Ti](Cl)(Cl)(Cl)Cl.C(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-carbaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, combined 282 mg of 6-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (1.37 mmol) with 10 ml of CH2Cl2 and chilled in ice-H2O bath. Added 4.1 ml of 1.0 M titanium tetrachloride in CH2Cl2 (4.1 mmol) dropwise. Stirred in cold for 1.5 hours. Added 186 μl of α,α-dichloromethyl methyl ether (2.06 mmol and stirred in cold for 15 minutes, then at room temperature overnight. Poured over ice-H2O, extracted three times with CH2Cl2. The combined organics were extracted with brine, sat. NaHCO3, brine, dried (MgSO4) and the solvent evaporated in vacuo to 289 mg of green solid (91%). 1H NMR (400 MHz, CDCl3) δ 1.35 (6H, s), 3.25 (3H, s), 3.98 (3H, s), 6.42 (1H, s), 7.68 (1H, s), 10.35 (1H, s), M/z (APCI+) 234.0 (M+1).

Workup

  1. stirringstirred in cold for 15 minutes
  2. customat room temperature
  3. customovernight
  4. extractionextracted three times with CH2Cl2
  5. extractionThe combined organics were extracted with brine, sat. NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated in vacuo to 289 mg of green solid (91%)

Sources & evidence

ORD record
ord-96a69d7f413c4a78bf1f7b5c4d8bf103
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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