2,2,2-trichloroethyl prop-2-enoate

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)-acetic acid (1.00 g, 6.61 mmol) and acrylic acid 2,2,2-trichloroethyl ester (6.73 g, 33.08 mmol) as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/MeOH 95:5 as the eluent to afford the product as an oil (1.17 g, 47.3%). 1H NMR (300 MHz, CDCl3): δ 7.17-7.33 (m, 4H), 4.73 (s, 2H), 4.52-4.56 (t, 1H), 3.60-3.63 (m, 2H), 3.37-3.42 (dd, 1H), 3.17-3.23 (dd, 1H). The crude product was purified by flash chromatography

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

Procedure: The title compound was prepared from 3-(4-amino phenyl)-propan-1-ol (1.02 g, 6.72 mmol) and acrylic acid 2,2,2-trichloroethylester (4.55 g, 22.17 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/iPrOH 95:5 as the eluent and the product was obtained as an oil (0.74 g, 29.4%). 1H NMR (300 MHz, CDCl3): δ 7.08-7.30 (m, 4H), 4.56-4.60 (t, 1H), 3.63-3.65 (m, 3H), 3.35-3.43 (dd, 1H), 3.18-3.25 (dd, 1H), 2.63-2.68 (m, 3H), 1.84-1.86 (m, 2H). The crude product was purified by flash chromatography

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)ethanol (6.68 g, 48.7 mmol) and commercially available acrylic acid 2,2,2-trichloroethylester (19.82 g, 97.44 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by repeated flash chromatography using DCM/MeOH 95:5 as the eluent and the product was obtained as an oil (1.87 g, 10.7%). 1H NMR (300 MHz, CDCl3): δ 7.15-7.29 (m, 4H), 4.54-4.59 (t, 1H), 3.82-3.85 (m, 3H), 3.38-3.45 (dd, 1H), 3.18-3.25 (dd, 1H), 2.79-2.87 (m, 3H). The crude product was purified by repeated flash chromatography

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)ethanol (6.68 g, 48.7 mmol) and commercially available acrylic acid 2,2,2-trichloroethylester (19.82 g, 97.44 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by repeated flash chromatography using DCM/MeOH 95:5 as the eluent and the product was obtained as an oil (1.87 g, 10.7%). 1H NMR (300 MHz, CDCl3): δ 7.15-7.29 (m, 4H), 4.54-4.59 (t, 1H), 3.82-3.85 (m, 3H), 3.38-3.45 (dd, 1H), 3.18-3.25 (dd, 1H), 2.79-2.87 (m, 3H). The crude product was purified by repeated flash chromatography

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

Procedure: A first solution including trichloroethanol (30 g, 201 mmol) and triethylamine (22.36 g, 221 mmol) dissolved in 50 g of diethylether was prepared. A second solution comprising acryloyl chloride (20 g, 221 mmol) dissolved in 50 g of diethylether was added dropwise to the first solution followed by stirring for four hours at room temperature. The resulting solution was then added to water, and the organic phase was extracted. The organic phase was distilled to yield 32.28 g of TCEA (78.9% yield). was prepared was added dropwise to the first solution the organic phase was extracted The organic phase was distilled

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

Procedure: A first solution including trichloroethanol (30 g, 201 mmol) and triethylamine (22.36 g, 221 mmol) dissolved in 50 g of diethylether was prepared. A second solution comprising acryloyl chloride (20 g, 221 mmol) dissolved in 50 g of diethylether was added dropwise to the first solution followed by stirring for four hours at room temperature. The resulting solution was then added to water, and the organic phase was extracted. The organic phase was distilled to yield 32.28 g of TCEA (78.9% yield). was prepared was added dropwise to the first solution the organic phase was extracted The organic phase was distilled

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

Procedure: A first solution including trichloroethanol (30 g, 201 mmol) and triethylamine (22.36 g, 221 mmol) dissolved in 50 g of diethylether was prepared. A second solution comprising acryloyl chloride (20 g, 221 mmol) dissolved in 50 g of diethylether was added dropwise to the first solution followed by stirring for four hours at room temperature. The resulting solution was then added to water, and the organic phase was extracted. The organic phase was distilled to yield 32.28 g of TCEA (78.9% yield). was prepared was added dropwise to the first solution the organic phase was extracted The organic phase was distilled

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

Procedure: A first solution including trichloroethanol (30 g, 201 mmol) and triethylamine (22.36 g, 221 mmol) dissolved in 50 g of diethylether was prepared. A second solution comprising acryloyl chloride (20 g, 221 mmol) dissolved in 50 g of diethylether was added dropwise to the first solution followed by stirring for four hours at room temperature. The resulting solution was then added to water, and the organic phase was extracted. The organic phase was distilled to yield 32.28 g of TCEA (78.9% yield). was prepared was added dropwise to the first solution the organic phase was extracted The organic phase was distilled

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)-acetic acid (1.00 g, 6.61 mmol) and acrylic acid 2,2,2-trichloroethyl ester (6.73 g, 33.08 mmol) as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/MeOH 95:5 as the eluent to afford the product as an oil (1.17 g, 47.3%). 1H NMR (300 MHz, CDCl3): δ 7.17-7.33 (m, 4H), 4.73 (s, 2H), 4.52-4.56 (t, 1H), 3.60-3.63 (m, 2H), 3.37-3.42 (dd, 1H), 3.17-3.23 (dd, 1H). The crude product was purified by flash chromatography

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

Procedure: The title compound was prepared from 3-(4-amino phenyl)-propan-1-ol (1.02 g, 6.72 mmol) and acrylic acid 2,2,2-trichloroethylester (4.55 g, 22.17 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/iPrOH 95:5 as the eluent and the product was obtained as an oil (0.74 g, 29.4%). 1H NMR (300 MHz, CDCl3): δ 7.08-7.30 (m, 4H), 4.56-4.60 (t, 1H), 3.63-3.65 (m, 3H), 3.35-3.43 (dd, 1H), 3.18-3.25 (dd, 1H), 2.63-2.68 (m, 3H), 1.84-1.86 (m, 2H). The crude product was purified by flash chromatography

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)ethanol (6.68 g, 48 7 mmol) and commercially available acrylic acid 2,2,2-trichloroethylester (19.82 g, 97.44 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by repeated flash chromatography using DCM/MeOH 95:5 as the eluent and the product was obtained as an oil (1.87 g, 10.7%). 1H NMR (300 MHz, CDCl3): δ 7.15-7.29 (m, 4H), 4.54-4.59 (t, 1H), 3.82-3.85 (m, 3H), 3.38-3.45 (dd, 1H), 3.18-3.25 (dd, 1H), 2.79-2.87 (m, 3H). The crude product was purified by repeated flash chromatography

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

Procedure: The title compound was prepared from 2-(4-amino phenyl)-acetic acid (1.00 g, 6.61 mmol) and acrylic acid 2,2,2-trichloroethyl ester (6.73 g, 33.08 mmol) as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/MeOH 95:5 as the eluent to afford the product as an oil (1.17 g, 47.3%). 1H NMR (300 MHz, CDCl3): δ 7.17-7.33 (m, 4H), 4.73 (s, 2H), 4.52-4.56 (t, 1H), 3.60-3.63 (m, 2H), 3.37-3.42 (dd, 1H), 3.17-3.23 (dd, 1H). The crude product was purified by flash chromatography