反应详情

温度

0 °C

Phosphorous oxychloride (0.42 g, 2.71 mmol) was added to DMF (0.99 g, 13.57 mmol) at 0° C. The resulting colorless solution was added dropwise to a solution of 2-(4-chloro-phenyl)-1H-indole4-carboxylic acid methyl ester (0.52 g, 1.81 mmol) in 10 mL dry CH2Cl2 at 0° C. The reaction was stirred at 0° C. for 10 min then quenched by addition of 5 mL 2 M NaOAc(aq). The layers were separated and the aqueous layer extracted once with CH2C12. The combined organic layers were dried (MgSO4) then concentrated in vacuo leaving an orange oil which crystallized on standing. The crystals were rinsed with CH2Cl2 then dried in vacuo to yield 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester, 231 mg (41%) as an off-white solid: m.p. 221-222° C.; 1H NMR (300 MHz, d6-DMSO) 3.93 (s, 3H), 7.49 (app t, J=7.5 Hz, 1H), 7.71 (m, 4H), 7.94 (d, J=7.8 Hz, 2H), 9.71 (s, 1H), 13.67 (br s, 1H). MS (electrospray, [M-H]) 312.

1. customthen quenched by addition of 5 mL 2 M NaOAc(aq)
2. customThe layers were separated
3. extractionthe aqueous layer extracted once with CH2C12
4. dry with materialThe combined organic layers were dried (MgSO4)
5. concentrationthen concentrated in vacuo
6. customleaving an orange oil which
7. customcrystallized
8. washThe crystals were rinsed with CH2Cl2
9. customthen dried in vacuo