1-methoxy-4-(2,2,2-trifluoroethyl)benzene

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

Procedure: This compound was prepared from Compound 83 in the same manner of Compound 45.

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

Procedure: To a stirred solution of Compound 45 (760 mg, 4.00 mmol) in dry CH2Cl2 (15 ml) was added TiCl4 (1.67 g, 8.80 mmol) via a syringe with ice-cooling. After 15 min, to this was added a solution of dichloromethyl methyl ether (920 mg, 8.00 mmol) in dry CH2Cl2 (5 ml) at same temperature. The reaction mixture was stirred at 0 C. for 15 min, and then for 1.5 h at room temperature. The mixture was diluted with water (20 ml) with ice-cooling and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with sat. NaHCO3 aq. and brine, dried (MgSO4), and concentrated in vacuo to give crude product as a yellow oil. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (40:1-20:1) to give Compound 46 (500 mg, 57%) as a colorless solid(needle). cooling for 15 min for 1.5 h at room temperature cooling stirred at room temperature for 15 min The organic layer was separated the aqueous layer was extracted with CH2Cl2 The combined solution was washed with sat. NaHCO3 aq. and brine dried (MgSO4) concentrated in vacuo to give crude product as a yellow oil The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (40:1-20:1)

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

Procedure: This compound was prepared from Compound 83 in the same manner of Compound 45.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of Compound 45 (760 mg, 4.00 mmol) in dry CH2Cl2 (15 ml) was added TiCl4 (1.67 g, 8.80 mmol) via a syringe with ice-cooling. After 15 min, to this was added a solution of dichloromethyl methyl ether (920 mg, 8.00 mmol) in dry CH2Cl2 (5 ml) at same temperature. The reaction mixture was stirred at 0° C. for 15 min, and then for 1.5 h at room temperature. The mixture was diluted with water (20 ml) with ice-cooling and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with sat. NaHCO3 aq. and brine, dried MgSO4), and concentrated in vacuo to give crude product as a yellow oil. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (40:1-20:1) to give Compound 46 (500 mg, 57%) as a colorless solid(needle). cooling for 1.5 h at room temperature cooling stirred at room temperature for 15 min The organic layer was separated the aqueous layer was extracted with CH2Cl2 The combined solution was washed with sat. NaHCO3 aq. and brine, dried MgSO4), and concentrated in vacuo to give crude product as a yellow oil The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (40:1-20:1)