ethyl 3-phenylprop-2-ynoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine and ethyl phenylpropiolate employing the procedure described in Example 76. [α]D25 +100.26 (c 0.507, DMSO).

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-amino-3-isopropyloxazolo[4,3-a]phthalazinium tetrafluoroborate (1.58 g) and ethyl phenylpropiolate (1.74 g) in 1,3-dimethyl-imidazolin-2-one (30 ml) was maintained at 40° C. for 19 hours and then the resulting brown solution was poured into water (200 ml), and the mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml). The extracts were combined, dried over magnesium sulphate, and evaporated, and the resulting residue was subjected to flash chromatography on silica gel, using as eluant a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v), to give ethyl 3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine-2-carboxylate (0.72 g) in the form of a yellow solid, m.p. 141°-142° C. [Elemental analysis: C, 77.1; H, 6.24; N, 7.8%; calculated C, 77.1; H, 6.19; N, 7.8%; NMR (in CDCl3) : 0.93 (3H, t, J=7 Hz), 1.57 (6H, d, J=7 Hz), 4.08 (2H, q, J=7 Hz), 4.35 (1H, septet, J=7 Hz), 7.23-7.50 (8H, m), 7.60-7.66 (1H, m), 8.35 (1H, s); Mass spectrum (electron impact) m/z=358]. the mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml) dried over magnesium sulphate evaporated a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-amino-3-isopropyloxazolo[4,3-a]phthalazinium tetrafluoroborate (1.58 g) and ethyl phenylpropiolate (1.74 g) in 1,3-dimethyl-imidazolin-2-one (30 ml) was maintained at 40° C. for 19 hours and then the resulting brown solution was poured into water (200 ml), and the mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml). The extracts were combined, dried over magnesium sulphate, and evaporated, and the resulting residue was subjected to flash chromatography on silica gel, using as eluant a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v), to give ethyl 3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine-2-carboxylate (0.72 g) in the form of a yellow solid, m.p. 141°-142° C. [Elemental analysis: C, 77.1; H, 6.24; N, 7.8%; calculated C, 77.1; H, 6.19; N, 7.8%; NMR (in CDCl3) : 0.93 (3H, t, J=7 Hz), 1.57 (6H, d, J=7 Hz), 4.08 (2H, q, J=7 Hz), 4.35 (1H, septet, J=7 Hz), 7.23-7.50 (8H, m), 7.60-7.66 (1H, m), 8.35 (1H, s); Mass spectrum (electron impact) m/z=358]. the mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml) dried over magnesium sulphate evaporated a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v)

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

Procedure: 78.5 g of anhydrous K2CO3 are added, in parts, to a solution of 40.5 g of ethyl phenylpropiolate and 43.5 g of chloropyrocatechol in 200 cc of anhydrous acetone. The mixture is heated for 15 h. It is subsequently filtered and the solvent eliminated at low pressure. The residue is treated as indicated in Example 2. The product has b.p. 150°-155°C/0.3 mm. The mixture is heated for 15 h It is subsequently filtered The residue is treated

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

Procedure: 78.5 g of anhydrous K2CO3 are added, in parts, to a solution of 40.5 g of ethyl phenylpropiolate and 43.5 g of chloropyrocatechol in 200 cc of anhydrous acetone. The mixture is heated for 15 h. It is subsequently filtered and the solvent eliminated at low pressure. The residue is treated as indicated in Example 2. The product has b.p. 150°-155°C/0.3 mm. The mixture is heated for 15 h It is subsequently filtered The residue is treated

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mix 4-Phenyl oxazole (3.33 g, 23.0 mmol) and ethyl phenylpropiolate (4.0 g, 23.0 mmol) in a sealed tube and heat at 220° C. for 20 hours. Perform flash-chromatography on silica gel eluting with 4:1 Hex/ethyl acetate to afford 3.9 g of 4-phenylfuran-3-carboxylic acid ethyl ester as a yellow oil. MS: m/e=217 (MH+).

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Added to 700 ml of toluene were 73.1 g (0.30 mole) of N-(2-chlorophenyl)-1-phenylpropaneimine, 34.8 g (0.20 mole) of ethyl phenylpropiolate and 40.0 g (0.30 mole) of aluminum chloride. The reaction mixture was then heated with stirring at 60° C. for 3 days. After cooling, the reaction mixture was poured into 1000 ml of 2N sulfuric acid, followed by extraction withchloroform. After washing the organic layer with water, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate). The crystals obtained were then recrystallized from a 1:2 mixed solvent of chloroform and hexane to give 17.0 of 1-(2-chlorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone.1/5HCl having a melting point of 229°-231° C. The reaction mixture was then heated After cooling followed by extraction withchloroform After washing the organic layer with water the organic layer was dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) The crystals obtained were then recrystallized from a 1:2 mixed solvent of chloroform and hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 300 ml of toluene were added 6.4 g (0.022 mole) of 1-(2-bromophenyl)-N-phenylpropaneimine, 3.9 g (0.022 mole) ethyl phenylpropiolate and 3.6 g (0.027 mole) of aluminum chloride. The reaction mixture was then heated at 60° C. hours. After cooling, the reaction mixture was poured into 500 ml of 2N sulfuric acid, followed by extraction with methylene chloride. After washing the organic layer (the extract) with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to chromatography on a silica gel column (eluent: ethyl acetate). The resultant crystals were then recrystallized from a 2:1 mixed solvent of acetone and hexane to obtain 1.3 g of 2-(2-bromophenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone hemihydrochloride having a melting point of 236°-238° C. After cooling followed by extraction with methylene chloride After washing the organic layer (the extract) with water the organic layer was dried over anhydrous sodium sulfate The solvent was distilled off The resultant crystals were then recrystallized from a 2:1 mixed solvent of acetone and hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 300 ml of toluene were added 6.4 g (0.022 mole) of 1-(2-bromophenyl)-N-phenylpropaneimine, 3.9 g (0.022 mole) ethyl phenylpropiolate and 3.6 g (0.027 mole) of aluminum chloride. The reaction mixture was then heated at 60° C. hours. After cooling, the reaction mixture was poured into 500 ml of 2N sulfuric acid, followed by extraction with methylene chloride. After washing the organic layer (the extract) with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to chromatography on a silica gel column (eluent: ethyl acetate). The resultant crystals were then recrystallized from a 2:1 mixed solvent of acetone and hexane to obtain 1.3 g of 2-(2-bromophenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone hemihydrochloride having a melting point of 236°-238° C. After cooling followed by extraction with methylene chloride After washing the organic layer (the extract) with water the organic layer was dried over anhydrous sodium sulfate The solvent was distilled off The resultant crystals were then recrystallized from a 2:1 mixed solvent of acetone and hexane

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

Procedure: To 300 ml of toluene were added 10.3 g (0.040 mole) of N-(2-chlorophenyl)-1-phenylbutaneimine, 5.2 g (0.030 mole) of ethyl phenylpropiolate and 5.3 g (0.040 mole) of aluminum chloride. After heating the reaction mixture under reflux for 20 hours under a nitrogen atmosphere, the reaction mixture was poured into 500 ml of 2N sulfuric acid which had been ice-cooled, followed by extraction with chloroform. After washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide and then with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) so that 2.0 g of 1-(2-chlorophenyl)-3-ethyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 165°-166° C. was obtained. After heating the reaction mixture under reflux for 20 hours under a nitrogen atmosphere cooled followed by extraction with chloroform After washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide with water, it was dried over anhydrous sodium sulfate Subsequent to removal of the sodium sulfate the solvent was distilled off the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) so that 2.0 g of 1-(2-chlorophenyl)-3-ethyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 165°-166° C. was obtained