propan-2-yl 3-phenylprop-2-enoate

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 homogeneous mixture containing cinnamaldehyde (7.5 mmol), Chloronil (22.5 mmol), isopropanol (10 mL) is taken in a round bottom flask and catalytic amount of silica gel (0.1 g) is added to it. The mixture is stirred for 20 hrs at room temperature. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with ethylacetate (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Isopropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C3H8) is isolated in 49% yield. 1H-NMR (CDCl3, 300 MHz) δ7.59 (1H, d, J=16.55 Hz), 7.41 (2H, m), 7.27 (3H, m), 6.34 (1H, d, J=16.55 Hz), 5.07 (1H, m), 1.18 (6H, d); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 144.3, 134.5, 130.1, 128.6, 128.0, 118.8, 67.7, 21.9. is taken in a round bottom flask catalytic amount of silica gel (0.1 g) is added to it After completion of the reaction (observed by TLC and by GC analysis) the reaction mixture is filtered washed with ethylacetate (5 ml×2) Concentrate the filtrate under reduced pressure the crude product thus obtained eluted with diethyl ether

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

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

Procedure: A homogeneous mixture containing cinnamaldehyde (7.5 mmol), Chloronil (22.5 mmol), isopropanol (10 mL) is taken in a round bottom flask and catalytic amount of silica gel (0.1 g) is added to it. The mixture is stirred for 20 hrs at room temperature. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with ethylacetate (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Isopropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C3H8) is isolated in 49% yield. 1H-NMR (CDCl3, 300 MHz) δ7.59 (1H, d, J=16.55 Hz), 7.41 (2H, m), 7.27 (3H, m), 6.34 (1H, d, J=16.55 Hz), 5.07 (1H, m), 1.18 (6H, d); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 144.3, 134.5, 130.1, 128.6, 128.0, 118.8, 67.7, 21.9. is taken in a round bottom flask catalytic amount of silica gel (0.1 g) is added to it After completion of the reaction (observed by TLC and by GC analysis) the reaction mixture is filtered washed with ethylacetate (5 ml×2) Concentrate the filtrate under reduced pressure the crude product thus obtained eluted with diethyl ether

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

Procedure: Lithium hydroxide-hydrate (236 mg, 5.63 mmol) and osmium tetroxide (53 mg, 0.210 mmol) are dissolved in a minimal amount of water. To this is added t-butanol (8 ml) and (DHQ)2PHAL (205 mg, 0.263 mmol) and the reaction mixture is stirred for 10 minutes. Water (12 mil) is added and the reaction mixture is cooled in an ice bath to less than 4°. Acetamide (311 mg, 5.26 mmol), isopropyl cinnamate (I, 1.00 g, 5.26 mmol), and N-bromoacetamide (795 mg, 5.63 mmol) respectively are added to the reaction mixture. The mixture is stirred until complete as measured by HPLC. The reaction mixture is quenched with a small amount of sodium sulfite (50 mg) and allowed to warm to 20-25°. Ethyl acetate (5 ml) is added and the reaction mixture is stirred for 30 minutes. The phases are separated and the aqueous layer is extracted three times with ethyl acetate (30 ml). The organic layers are combined and washed three times with saline (30 ml). The organic layer is dried with sodium sulfate and filtered through a small amount of silica. The mixture is concentrated on a rotary evaporator and the product is recrystallized from ethyl acetate/hexane to give the title compound; mp=104-106°; HMR (300 MHz, CDCl3) 1.30, 2.00, 3.20, 4.78, 5.05, 5.55, 6.23 and 7.35 δ. the reaction mixture is cooled in an ice bath to less than 4° The mixture is stirred until complete The reaction mixture is quenched with a small amount of sodium sulfite (50 mg) to warm to 20-25° Ethyl acetate (5 ml) is added the reaction mixture is stirred for 30 minutes The phases are separated the aqueous layer is extracted three times with ethyl acetate (30 ml) washed three times with saline (30 ml) The organic layer is dried with sodium sulfate filtered through a small amount of silica The mixture is concentrated on a rotary evaporator the product is recrystallized from ethyl acetate/hexane

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

Procedure: A homogeneous mixture containing cinnamaldehyde (7.5 mmol), Chloronil (22.5 mmol), isopropanol (10 mL) is taken in a round bottom flask and catalytic amount of silica gel (0.1 g) is added to it. The mixture is stirred for 20 hrs at room temperature. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with ethylacetate (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Isopropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C3H8) is isolated in 49% yield. 1H-NMR (CDCl3, 300 MHz) δ7.59 (1H, d, J=16.55 Hz), 7.41 (2H, m), 7.27 (3H, m), 6.34 (1H, d, J=16.55 Hz), 5.07 (1H, m), 1.18 (6H, d); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 144.3, 134.5, 130.1, 128.6, 128.0, 118.8, 67.7, 21.9. is taken in a round bottom flask catalytic amount of silica gel (0.1 g) is added to it After completion of the reaction (observed by TLC and by GC analysis) the reaction mixture is filtered washed with ethylacetate (5 ml×2) Concentrate the filtrate under reduced pressure the crude product thus obtained eluted with diethyl ether