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

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Reaction Steps

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).

Provenance & Evidence