4-prop-2-enylbenzaldehyde

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: 5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2). at room temperature The mixture was concentrated under high vacuum The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

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

Procedure: 5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2). at room temperature The mixture was concentrated under high vacuum The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

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

Procedure: 5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2). at room temperature The mixture was concentrated under high vacuum The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

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

Procedure: 5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2). at room temperature The mixture was concentrated under high vacuum The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

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

Procedure: 5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2). at room temperature The mixture was concentrated under high vacuum The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

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

Procedure: To a solution of 834 mg of 2'-(1-carboxymethoxy)-4'-(3-methyl-2-butenyloxy)acetophenone and 500 mg of 4-(2-propenyl)benzaldehyde in 10 ml of ethanol was added 842 mg of potassium hydroxide, and the mixture was stirred for 20 minutes. After neutralization with dilute hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate - n-hexane to give 360 mg of the title compound as a pale yellow needles. After neutralization with dilute hydrochloric acid, the mixture was extracted with ethyl acetate The organic layer was washed with water dried the solvent was evaporated under reduced pressure The residue was recrystallized from ethyl acetate - n-hexane