反应详情

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).

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%)