ethyl 3-chlorobenzoate

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: The title compound is prepared as described in Example 1 using 3-chloro-benzoic acid ethyl ester (see Example 5) and 4-(2-diethylamino-ethoxy)-phenylamine (see Example 3).

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

実験手順: The title compound is prepared as described in Example 1 using 3-chloro-benzoic acid ethyl ester (see Example 5) and 4-(2-diethylamino-ethoxy)-phenylamine (see Example 3).

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

実験手順: To a cold (0° C.) solution of 4-methylpyrimidine (4.56 mL 50.1 mmol) and ethyl 3-chlorobenzoate (7.90 mL 50.1 mmol) in tetrahydrofuran (50 mL) was added lithium bis(trimethylsilyl)amide (100 mL, 1.0M in tetrahydrofuran, 100 mmol) dropwise over 30 minutes. The resultant mixture was warmed to room temperature and stirred 16 hours. The reaction mixture was concentrated in vacuo. The resultant oil was diluted with methanol. Upon standing, a solid precipitated, which was collected on a filter to provide 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethenol (11.2 g, 93%) as a yellow solid. Rf 0.31 (3:1 hexanes:ethyl acetate); 1H NMR (d6-DMSO) δ 8.37 (s, 1H), 7.98 (m, 1H), 7.81–7.76 (m, 2H), 7.38–7.32 (m, 2H), 6.71 (br, 1H), 5.65 (s, 1H); MS m/z 233 (M+1). The reaction mixture was concentrated in vacuo The resultant oil was diluted with methanol a solid precipitated which was collected on a filter

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

実験手順: The title compound is prepared as described in Example 1 using 3-chloro-benzoic acid ethyl ester (see Example 5) and 4-(2-diethylamino-ethoxy)-phenylamine (see Example 3).