1-(2-chlorophenyl)-2,2,2-trifluoroethanone

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: 1-(2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (63 mg, 0.095 mmol) and 1-(2-chlorophenyl)-2,2,2-trifluoroethanone following General Procedure B. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (43 mg, 83%): 1H NMR (CDCl3, 600 MHz) δ 7.70-7.64 (m, 3H), 7.51-7.48 (m, 1H), 7.26-7.24 (m, 3H), 7.16-7.15 (m, 3H), 4.79 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.88-1.81 (m, 2H), 1.61-1.60 (m, 2H), 1.35-1.25 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.05 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.2 (d, J=35 Hz), 167.0, 149.4, 143.7, 133.6, 133.6, 131.1, 129.5, 129.4, 129.3, 129.1, 128.3, 126.4, 125.6, 116.4 (d, J=285 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.5, 26.5, 25.8, 19.0, −4.2, −4.4.

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

Procedure: 1-(2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (63 mg, 0.095 mmol) and 1-(2-chlorophenyl)-2,2,2-trifluoroethanone following General Procedure B. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (43 mg, 83%): 1H NMR (CDCl3, 600 MHz) δ 7.70-7.64 (m, 3H), 7.51-7.48 (m, 1H), 7.26-7.24 (m, 3H), 7.16-7.15 (m, 3H), 4.79 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.88-1.81 (m, 2H), 1.61-1.60 (m, 2H), 1.35-1.25 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.05 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.2 (d, J=35 Hz), 167.0, 149.4, 143.7, 133.6, 133.6, 131.1, 129.5, 129.4, 129.3, 129.1, 128.3, 126.4, 125.6, 116.4 (d, J=285 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.5, 26.5, 25.8, 19.0, −4.2, −4.4.

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

Procedure: 1-(2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (63 mg, 0.095 mmol) and 1-(2-chlorophenyl)-2,2,2-trifluoroethanone following General Procedure B. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (43 mg, 83%): 1H NMR (CDCl3, 600 MHz) δ 7.70-7.64 (m, 3H), 7.51-7.48 (m, 1H), 7.26-7.24 (m, 3H), 7.16-7.15 (m, 3H), 4.79 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.88-1.81 (m, 2H), 1.61-1.60 (m, 2H), 1.35-1.25 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.05 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.2 (d, J=35 Hz), 167.0, 149.4, 143.7, 133.6, 133.6, 131.1, 129.5, 129.4, 129.3, 129.1, 128.3, 126.4, 125.6, 116.4 (d, J=285 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.5, 26.5, 25.8, 19.0, −4.2, −4.4.