3-(4-methoxyphenyl)prop-2-enal

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

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

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: A mixture of 4-methoxy phenylpropane (2 g), silica gel (0.5-0.8 g), DDQ (7.5 g) and dioxane (5-8 ml) was taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was placed inside a microwave oven operating at medium power (600 W) and irradiated for 2-8 minutes. After completion of the reaction (monitored by TLC), the contents of the flask were poured into chloroform and passed through a bed of Celite and further washed with chloroform. The filtrate and washing were combined and the chloroform layers were washed with an aqueous NaOH (15%, 3×15 ml). The combined aqueous layers were further extracted with chloroform (3×15 ml). The chloroform layers were then combined and washed with saturated sodium chloride (3×15 m), dried over anhydrous sodium sulphate and filtered. The solvent was removed to afford a crude product which was loaded on silica column and the column was first eluted with hexane (70-80 ml) and then with an increasing amount of hexane/ethyl acetate (9:1 to 1:9). The fractions were monitored on TLC plate and the desired fractions were combined and solvent was removed under vacuum to afford 4-methoxy cinnamaldehyde in 68% yield as a solid; mp 57-58° C.; (lit. mp 58° C.). The physical and spectral data was found to similar as reported. fitted with a loose funnel at the top The flask was placed inside a microwave oven operating at medium power (600 W) and irradiated for 2-8 minutes After completion of the reaction (monitored by TLC) further washed with chloroform The filtrate and washing the chloroform layers were washed with an aqueous NaOH (15%, 3×15 ml) The combined aqueous layers were further extracted with chloroform (3×15 ml) washed with saturated sodium chloride (3×15 m) dried over anhydrous sodium sulphate filtered The solvent was removed to afford a crude product which the column was first eluted with hexane (70-80 ml) solvent was removed under vacuum

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

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

Procedure: 16.5 g of an 80% by weight suspension of sodium hydride in white oil (corresponding to 0.55 mol of NaH) were mixed with 500 ml of anhydrous tetrahydrofuran and, while stirring efficiently at 50° to 60° C., a mixture of 81 g (corresponding to 0.5 mol) of p-methoxycinnamaldehyde and 65 g (corresponding to 0.5 mol) of methyl β-methoxycrotonate was added dropwise. The rate of this dropwise addition was chosen so that the mixture continued to boil gently. It was then stirred at 65° C. for 3 hours and subsequently at room temperature overnight. To work up the reaction mixture was cooled and mixed with 0.5 l of ice-water and then extracted with methyl tertbutyl ether. The remaining alkaline aqueous phase was acidified with dilute hydrochloric acid while cooling in ice, and the precipitate was filtered off and thoroughly washed with water. Drying resulted in 83 g of the title compound of melting point 187° C. (after recrystallization from ethyl acetate), corresponding to a yield of 64%. was added dropwise The rate of this dropwise addition It was then stirred at 65° C. for 3 hours and subsequently at room temperature overnight was cooled extracted with methyl tertbutyl ether while cooling in ice the precipitate was filtered off thoroughly washed with water Drying

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

Procedure: To 0.52 g (3.2 mmol) of the aldehyde from step (a) and 0.26 g (4 mmol) malononitrile in 30 ml ethanol was added 2 drops piperidine and the reaction mixture was refluxed for 40 minutes, cooled, filtered and washed with ethanol to yield 0.61 g (90% yield) of an orange solid, m.p. 160° C. the reaction mixture was refluxed for 40 minutes cooled filtered washed with ethanol

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

Procedure: To 0.52 g (3.2 mmol) of the aldehyde from step (a) and 0.26 g (4 mmol) malononitrile in 30 ml ethanol was added 2 drops piperidine and the reaction mixture was refluxed for 40 minutes, cooled, filtered and washed with ethanol to yield 0.61 g (90% yield) of an orange solid, m.p. 160° C. the reaction mixture was refluxed for 40 minutes cooled filtered washed with ethanol

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2 g (12.6 mmol) 4-methoxycinnamonitrile in 10:10:20 ml H2O:HOAc:pyridine was added 5 g (47 mmol) NaH2PO2 (hypophosphite) followed by 2 g RaNi. After stirring 3 hours at 50° C., the reaction mixture was filtered, extracted with CH2Cl2, washed with dilute HCl, washed with H2O and evaporated to give 0.7 g (35% yield) 4-methoxycinnamaldehyde, a yellow solid, m.p. 47° C. the reaction mixture was filtered extracted with CH2Cl2 washed with dilute HCl washed with H2O evaporated

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

Procedure: N-Acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline, ethyl ester (13 g, 72%) was prepared from 4-methoxycinnamaldehyde (Lancaster, 8.1 g, 50 mmol) and diethyl acetamidomalonate (Aldrich, 9.9 g, 45 mmol) by the procedure described by Chung et al (J. Org. Chem. 1990, 55, 270).

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

Procedure: A mixture of 4-methoxy phenylpropane (2 g), silica gel (0.5-0.8 g), DDQ (7.5 g) and dioxane (5-8 ml) was taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was placed inside a microwave oven operating at medium power (600 W) and irradiated for 2-8 minutes. After completion of the reaction (monitored by TLC), the contents of the flask were poured into chloroform and passed through a bed of Celite and further washed with chloroform. The filtrate and washing were combined and the chloroform layers were washed with an aqueous NaOH (15%, 3×15 ml). The combined aqueous layers were further extracted with chloroform (3×15 ml). The chloroform layers were then combined and washed with saturated sodium chloride (3×15 m), dried over anhydrous sodium sulphate and filtered. The solvent was removed to afford a crude product which was loaded on silica column and the column was first eluted with hexane (70-80 ml) and then with an increasing amount of hexane/ethyl acetate (9:1 to 1:9). The fractions were monitored on TLC plate and the desired fractions were combined and solvent was removed under vacuum to afford 4-methoxy cinnamaldehyde in 68% yield as a solid; mp 57-58° C.; (lit. mp 58° C.). The physical and spectral data was found to similar as reported. fitted with a loose funnel at the top The flask was placed inside a microwave oven operating at medium power (600 W) and irradiated for 2-8 minutes After completion of the reaction (monitored by TLC) further washed with chloroform The filtrate and washing the chloroform layers were washed with an aqueous NaOH (15%, 3×15 ml) The combined aqueous layers were further extracted with chloroform (3×15 ml) washed with saturated sodium chloride (3×15 m) dried over anhydrous sodium sulphate filtered The solvent was removed to afford a crude product which the column was first eluted with hexane (70-80 ml) solvent was removed under vacuum