ethyl 2-(3-formyl-1H-indol-2-yl)acetate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl (3-formylindolyl)acetate (15.9 g) was dissolved in 1,4-dioxane (100 ml) and added 36% aq. NaOH (10 ml). The resulting mixture was stirred at room temperature for 4 days. Water (500 ml) was added and the mixture was washed with diethyl ether (150 ml). The aqueous phase was made acidic with 5N HCl and extracted with ethyl acetate (250+150 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford 10.3 g (73% over two steps) of (3-formylindolyl)acetic acid. the mixture was washed with diethyl ether (150 ml) extracted with ethyl acetate (250+150 ml) The combined organic extracts were dried (MgSO4) evaporated in vacuo

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Formylindole (10.0 g, 69 mmoles) was dissolved in DMF (100 ml). Under N2 was a 60% suspension of NaH in mineral oil (3.0 g) added in portions with cooling (temp<15° C.). At <15° C. was a solution of ethyl bromoacetate (8.4 ml) in DMF (15 ml) added drop wise over 30 minutes. The resulting mixture was stirred at room temperature for 16 hours and evaporated in vacuo. The residue was added water (300 ml) and extracted with ethyl acetate (2×150 ml), the combined organic extracts were washed with satd. NH4Cl, dried (MgSO4) and concentrated to afford 15.9 g ethyl (3-formylindolyl)acetate. added in portions At <15° C. added drop wise over 30 minutes evaporated in vacuo The residue was added water (300 ml) extracted with ethyl acetate (2×150 ml) the combined organic extracts were washed with satd NH4Cl, dried (MgSO4) concentrated

反応条件: temp:0.00; pressure:0.00; stir: