HEPTANOPHENONE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane, 25 mmol of heptanophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction, a solid precipitated out which was triturated with ether and filtered (m.p. 119°-120.5° C.). 1H NMR (CDCl3) δ 0.84 (t, 3 H), 1.1-1.4 (m, 8 H), 1.9-2.0 (m, 2 H), 2.89 (d, 1 H), 2.93 (d, 1 H), 3.24 (d, 1 H), 3.35 (d, 1 H), 7.2-7.5 (m, 5 H). Upon concentrating the reaction a solid precipitated out which was triturated with ether filtered (m.p. 119°-120.5° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 1 0.01 mmol. While the reactor was stopped with a stopper, the reactants were stirred at various temperatures (70-130° C.) as shown in the following table 10 for 1 hour. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various temperatures and the results are given in Table 10, below. the reactants were stirred at various temperatures (70-130° C.) as shown in the following table 10 for 1 hour After completion of the reaction, gas chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 1 0.01 mmol. While the reactor was stopped with a stopper, the reactants were stirred at various temperatures (70-130° C.) as shown in the following table 10 for 1 hour. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various temperatures and the results are given in Table 10, below. the reactants were stirred at various temperatures (70-130° C.) as shown in the following table 10 for 1 hour After completion of the reaction, gas chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were stirred at 130 ° C. for various reaction times as shown in the following table 9. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various period of times and the results are given in Table 9, below. the reactants were stirred at 130 ° C. for various reaction times After completion of the reaction, gas chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were stirred at 130 ° C. for various reaction times as shown in the following table 9. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various period of times and the results are given in Table 9, below. the reactants were stirred at 130 ° C. for various reaction times After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol), 1-hexene and toluene at various amounts as shown in the following table 8, were added to each 500 ml pressure reactor. The mixture was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were heated at 130 ° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to 1-hexene and toluene of various amounts. The results are given in Table 8, below. were added to each 500 ml pressure reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol), 1-hexene and toluene at various amounts as shown in the following table 8, were added to each 500 ml pressure reactor. The mixture was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were heated at 130 ° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to 1-hexene and toluene of various amounts. The results are given in Table 8, below. were added to each 500 ml pressure reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then [Rh(C8H14)2Cl]2 0.01 mmol and various phosphine ligands 0.025 mmol as shown in the following table 7 were introduced into each reactor. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products from various phosphine ligands. The results are given in Table 7, below. were introduced into each reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then [Rh(C8H14)2Cl]2 0.01 mmol and various phosphine ligands 0.025 mmol as shown in the following table 7 were introduced into each reactor. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products from various phosphine ligands. The results are given in Table 7, below. were introduced into each reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then various transition metal catalysts as shown in the following table 6 were added to each reactor. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various transition metal catalysts. The results are shown in Table 6, below. were added to each reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then various transition metal catalysts as shown in the following table 6 were added to each reactor. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products according to various transition metal catalysts. The results are shown in Table 6, below. were added to each reactor with stirring After completion of the reaction, gas chromatography

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), various kinds of amines 0.3 mmol as shown in the following table 5, were added to each 500 ml pressure reactor. The mixture was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, column chromatography was conducted to determine the yields of heptanophenone, products according to various amines. The results are given in Table 5, below. were added to each 500 ml pressure reactor with stirring After completion of the reaction, column chromatography