ethyl (E)-3-(2,4-dichlorophenyl)prop-2-enoate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (sat. aq., 70 ml) was then added and the reaction allowed to warm to 0° C. After 15 min at 0° C. the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was then filtered through a pad of hyflo supercel (washing well with ethyl acetate) and the concentrated to give the title compound (7.8 g) as pale yellow crystals. 1H NMR δ (ppm)(CDCl3): 7.44 (1 H, d, J=8.4 Hz), 7.36 (1 H, d, J=2.0 Hz), 7.19 (1 H, dd, J=2.0, 8.5 Hz), 6.93 (1 H, d, J=15.8 Hz), 6.36-6.28 (1 H, m), 4.35 (2 H, d, J=5.4 Hz), 1.84 (1 H, s). After addition to warm to 0° C to warm to room temperature The mixture was then filtered through a pad of hyflo supercel ( washing well with ethyl acetate) and the concentrated

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

Procedure: To a stirred solution of (2E)-3-(2,4-Dichlorophenyl)acrylic acid (10 g, 46 mmol) in ethanol (60 ml) was added conc. H2SO4 (2.5 ml). The mixture was heated to reflux and for 48 H, then allowed to cool, concentrated in vacuo, dissolved in ethyl acetate, washed three times with 4N NaOH, dried over sodium sulfate and concentrated in vacuo to afford ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (10.7 g) as pale brown crystals. 1H NMR δ (ppm)(CDCl3): 8.00 (1 H, d, J=16.1 Hz), 7.55 (1 H, d, J=8.5 Hz), 7.44 (1 H, d, J=1.9 Hz), 7.26 (1 H, dd, J=2.0, 8.4 Hz), 6.41 (1 H, d, J=16.1 Hz), 4.28 (2 H, q, J=7.1 Hz), 1.34 (3 H, t, J=7.1 Hz). The mixture was heated to reflux and for 48 H to cool concentrated in vacuo dissolved in ethyl acetate washed three times with 4N NaOH dried over sodium sulfate concentrated in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (sat. aq., 70 ml) was then added and the reaction allowed to warm to 0° C. After 15 min at 0° C. the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was then filtered through a pad of hyflo supercel (washing well with ethyl acetate) and the concentrated to give the title compound (7.8 g) as pale yellow crystals. 1H NMR δ (ppm)(CDCl3): 7.44 (1 H, d, J=8.4 Hz), 7.36 (1 H, d, J=2.0 Hz), 7.19 (1 H, dd, J=2.0, 8.5 Hz), 6.93 (1 H, d, J=15.8 Hz), 6.36-6.28 (1 H, m), 4.35 (2 H, d, J=5.4 Hz), 1.84 (1 H, s). After addition to warm to 0° C to warm to room temperature The mixture was then filtered through a pad of hyflo supercel ( washing well with ethyl acetate) and the concentrated

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

Procedure: To a stirred solution of (2E)-3-(2,4-Dichlorophenyl)acrylic acid (10 g, 46 mmol) in ethanol (60 ml) was added conc. H2SO4 (2.5 ml). The mixture was heated to reflux and for 48 H, then allowed to cool, concentrated in vacuo, dissolved in ethyl acetate, washed three times with 4N NaOH, dried over sodium sulfate and concentrated in vacuo to afford ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (10.7 g) as pale brown crystals. 1H NMR δ (ppm)(CDCl3): 8.00 (1 H, d, J=16.1 Hz), 7.55 (1 H, d, J=8.5 Hz), 7.44 (1 H, d, J=1.9 Hz), 7.26 (1 H, dd, J=2.0, 8.4 Hz), 6.41 (1 H, d, J=16.1 Hz), 4.28 (2 H, q, J=7.1 Hz), 1.34 (3 H, t, J=7.1 Hz). The mixture was heated to reflux and for 48 H to cool concentrated in vacuo dissolved in ethyl acetate washed three times with 4N NaOH dried over sodium sulfate concentrated in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (sat. aq., 70 ml) was then added and the reaction allowed to warm to 0° C. After 15 min at 0° C. the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was then filtered through a pad of hyflo supercel (washing well with ethyl acetate) and the concentrated to give the title compound (7.8 g) as pale yellow crystals. 1H NMR δ (ppm)(CDCl3): 7.44 (1 H, d, J=8.4 Hz), 7.36 (1 H, d, J=2.0 Hz), 7.19 (1 H, dd, J=2.0, 8.5 Hz), 6.93 (1 H, d, J=15.8 Hz), 6.36-6.28 (1 H, m), 4.35 (2 H, d, J=5.4 Hz), 1.84 (1 H, s). After addition to warm to 0° C to warm to room temperature The mixture was then filtered through a pad of hyflo supercel ( washing well with ethyl acetate) and the concentrated

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

Procedure: To a stirred solution of (2E)-3-(2,4-Dichlorophenyl)acrylic acid (10 g, 46 mmol) in ethanol (60 ml) was added conc. H2SO4 (2.5 ml). The mixture was heated to reflux and for 48 H, then allowed to cool, concentrated in vacuo, dissolved in ethyl acetate, washed three times with 4N NaOH, dried over sodium sulfate and concentrated in vacuo to afford ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (10.7 g) as pale brown crystals. 1H NMR δ (ppm)(CDCl3): 8.00 (1 H, d, J=16.1 Hz), 7.55 (1 H, d, J=8.5 Hz), 7.44 (1 H, d, J=1.9 Hz), 7.26 (1 H, dd, J=2.0, 8.4 Hz), 6.41 (1 H, d, J=16.1 Hz), 4.28 (2 H, q, J=7.1 Hz), 1.34 (3 H, t, J=7.1 Hz). The mixture was heated to reflux and for 48 H to cool concentrated in vacuo dissolved in ethyl acetate washed three times with 4N NaOH dried over sodium sulfate concentrated in vacuo