ethyl 3-oxo-5-phenylpent-4-enoate

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

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added over a period of 10 minutes to a cold (5°) solution of 0.015 moles of ethyl acetoacetate and 0.015 moles of benzaldehyde in 60 ml of tetrahydrofuran. After the mixture was stirred for 1.5 hours, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours

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

Procedure: To a cold (5°) solution of 0.015 moles of benzaldehyde and 0.015 moles of ethyl acetoacetate in 60 ml of tetrahydrofuran was added 0.060 mole of triethylamine. After the mixture was stirred for 5 minutes, a solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added dropwise over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title product was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added to a cold (0°) solution of 0.015 moles of ethyl acetoacetate in 75 ml of tetrahydrofuran. After the mixture was stirred for 15 minutes, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise over five minutes. After the mixture was stirred an additional 15 minutes, a solution of 0.015 moles of benzaldehyde in 15 ml of tetrahydrofuran was added over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. After the mixture was stirred an additional 15 minutes The reaction mixture was then stirred for 20 hours

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 5 ml of carbon tetrachloride was added dropwise at room temperature to 50 ml of dichloromethane. The mixture was cooled to 0° and a solution of 0.020 moles of N,N,N',N'-tetramethylethylenediamine in 5 ml of dichloromethane was added dropwise over 15 minutes. After the mixture was stirred an additional hour, a solution of 0.015 moles of ethyl acetoacetate in 10 ml of dichloromethane was added dropwise over 15 minutes. After the mixture was stirred an additional hour, a solution of 0.030 moles of triethylamine in 15 ml of dichloromethane was added over 10 minutes. After thirty minutes, a solution of 0.015 moles of benzaldehyde in 10 ml of dichloromethane was added over 10 minutes. The reaction mixture was stirred for 20 hours. Water (25 ml) was added and the resultant two-phase mixture was stirred for two hours. After the layers were separated, the aqueous layer was extracted with 50 ml of ethyl acetate. The ethyl acetate extract was combined with the initially separated organic layer, dried over sodium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel gave the title compound as a solid. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The mixture was cooled to 0° After the mixture was stirred an additional hour After thirty minutes The reaction mixture was stirred for 20 hours After the layers were separated the aqueous layer was extracted with 50 ml of ethyl acetate The ethyl acetate extract dried over sodium sulfate filtered concentrated in vacuo to an oil

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added over a period of 10 minutes to a cold (5°) solution of 0.015 moles of ethyl acetoacetate and 0.015 moles of benzaldehyde in 60 ml of tetrahydrofuran. After the mixture was stirred for 1.5 hours, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours

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

Procedure: To a cold (5°) solution of 0.015 moles of benzaldehyde and 0.015 moles of ethyl acetoacetate in 60 ml of tetrahydrofuran was added 0.060 mole of triethylamine. After the mixture was stirred for 5 minutes, a solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added dropwise over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title product was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added to a cold (0°) solution of 0.015 moles of ethyl acetoacetate in 75 ml of tetrahydrofuran. After the mixture was stirred for 15 minutes, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise over five minutes. After the mixture was stirred an additional 15 minutes, a solution of 0.015 moles of benzaldehyde in 15 ml of tetrahydrofuran was added over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. After the mixture was stirred an additional 15 minutes The reaction mixture was then stirred for 20 hours

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 5 ml of carbon tetrachloride was added dropwise at room temperature to 50 ml of dichloromethane. The mixture was cooled to 0° and a solution of 0.020 moles of N,N,N',N'-tetramethylethylenediamine in 5 ml of dichloromethane was added dropwise over 15 minutes. After the mixture was stirred an additional hour, a solution of 0.015 moles of ethyl acetoacetate in 10 ml of dichloromethane was added dropwise over 15 minutes. After the mixture was stirred an additional hour, a solution of 0.030 moles of triethylamine in 15 ml of dichloromethane was added over 10 minutes. After thirty minutes, a solution of 0.015 moles of benzaldehyde in 10 ml of dichloromethane was added over 10 minutes. The reaction mixture was stirred for 20 hours. Water (25 ml) was added and the resultant two-phase mixture was stirred for two hours. After the layers were separated, the aqueous layer was extracted with 50 ml of ethyl acetate. The ethyl acetate extract was combined with the initially separated organic layer, dried over sodium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel gave the title compound as a solid. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The mixture was cooled to 0° After the mixture was stirred an additional hour After thirty minutes The reaction mixture was stirred for 20 hours After the layers were separated the aqueous layer was extracted with 50 ml of ethyl acetate The ethyl acetate extract dried over sodium sulfate filtered concentrated in vacuo to an oil

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

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

Procedure: A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added over a period of 10 minutes to a cold (5°) solution of 0.015 moles of ethyl acetoacetate and 0.015 moles of benzaldehyde in 60 ml of tetrahydrofuran. After the mixture was stirred for 1.5 hours, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours

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

Procedure: To a cold (5°) solution of 0.015 moles of benzaldehyde and 0.015 moles of ethyl acetoacetate in 60 ml of tetrahydrofuran was added 0.060 mole of triethylamine. After the mixture was stirred for 5 minutes, a solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added dropwise over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title product was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2. The reaction mixture was then stirred for 20 hours