(2-methoxyphenoxy)-tri(propan-2-yl)silane

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

Procedure: nBuLi (2.5 M in hexanes) (36 mmol) is mixed with TMEDA (36 mmol) at 0° C. in a dry round bottom flask for 10 minutes. A solution of triisopropyl-(2-methoxy-phenoxy)-silane (24 mmol) in 25 mL of dry THF is added to the above mixture. The mixture is warmed up to room temperature in 2 hours by removal of the ice bath. The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature. The mixture is stirred overnight. HCl (1 M) is added to the mixture to quench the reaction. The mixture is diluted with EtOAc (100 mL), washed with HCl (1 M) (2×100 mL) and brine (50 mL) and finally dried over anhydrous Na2SO4. Purification is accomplished by silica flash chromatography (5% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as a colorless oil which needs to be stored at low temperatures: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 7.42 (dd, J1=7.7 Hz, J2=1.7 Hz, 1H), 7.67 (d, J1=8 Hz, J2=1.7 Hz, 1H), 7.04 (t, J=8.4 Hz, 1H), 3.96 (s, 3H), 1.26-1.35 (m, 3H), 1.13 (s, 9H), 1.12 (s, 9H). LC/MS (ES+): (M+1) 309.2. Rf=0.4 (5% EtOAc/hexane). The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature HCl (1 M) is added to the mixture to quench the reaction washed with HCl (1 M) (2×100 mL) and brine (50 mL) finally dried over anhydrous Na2SO4 Purification

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Guaiacol (2-methoxy-phenol, 34.6 mmol) is mixed with TIPSCl (51.9 mmol) and imidazole (103.8 mmol) in a tube. The mixture is heated in the microwave oven at 180° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying over anhydrous Na2SO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield triisopropyl-(2-methoxy-phenoxy)-silane as a colorless oil. Yield: 69%. 1H NMR (400 MHz, CDCl3) δ 6.8-6.89 (m, 4H), 3.8 (s, 3H), 1.22-1.28 (m, 3H), 1.1 (s, 9H), 1.08 (s, 9H). LC/MS (ES+): (M+1), 281.2. Rf=0.8 (5% EtOAc/hexane). (Note: Alternatively, conventional heating might be adopted in which case NMP is the solvent of choice). washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL) After drying over anhydrous Na2SO4 the filtrate is concentrated The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Guaiacol (2-methoxy-phenol, 34.6 mmol) is mixed with TIPSCl (51.9 mmol) and imidazole (103.8 mmol) in a tube. The mixture is heated in the microwave oven at 180° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying over anhydrous Na2SO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield triisopropyl-(2-methoxy-phenoxy)-silane as a colorless oil. Yield: 69%. 1H NMR (400 MHz, CDCl3) δ 6.8-6.89 (m, 4H), 3.8 (s, 3H), 1.22-1.28 (m, 3H), 1.1 (s, 9H), 1.08 (s, 9H). LC/MS (ES+): (M+1), 281.2. Rf=0.8 (5% EtOAc/hexane). (Note: Alternatively, conventional heating might be adopted in which case NMP is the solvent of choice). washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL) After drying over anhydrous Na2SO4 the filtrate is concentrated The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)

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

Procedure: nBuLi (2.5 M in hexanes) (36 mmol) is mixed with TMEDA (36 mmol) at 0° C. in a dry round bottom flask for 10 minutes. A solution of triisopropyl-(2-methoxy-phenoxy)-silane (24 mmol) in 25 mL of dry THF is added to the above mixture. The mixture is warmed up to room temperature in 2 hours by removal of the ice bath. The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature. The mixture is stirred overnight. HCl (1 M) is added to the mixture to quench the reaction. The mixture is diluted with EtOAc (100 mL), washed with HCl (1 M) (2×100 mL) and brine (50 mL) and finally dried over anhydrous Na2 SO4. Purification is accomplished by silica flash chromatography (5% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as a colorless oil which needs to be stored at low temperatures: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 7.42 (dd, J1=7.7 Hz, J2=1.7 Hz, 1H), 7.67 (d, J1=8 Hz, J2=1.7 Hz, 1H), 7.04 (t, J=8.4 Hz, 1H), 3.96 (s, 3H), 1.26-1.35 (m, 3H), 1.13 (s, 9H), 1.12 (s, 9H). LC/MS (ES+): (M+1) 309.2. Rf=0.4 (5% EtOAc/hexane). The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature HCl (1 M) is added to the mixture to quench the reaction washed with HCl (1 M) (2×100 mL) and brine (50 mL) finally dried over anhydrous Na2 SO4 Purification

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Guaiacol (2-methoxy-phenol, 34.6 mmol) is mixed with TIPSCl (51.9 mmol) and imidazole (103.8 mmol) in a tube. The mixture is heated in the microwave oven at 180° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying over anhydrous Na2SO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield triisopropyl-(2-methoxy-phenoxy)-silane as a colorless oil. Yield: 69%. 1H NMR (400 MHz, CDCl3) δ 6.8-6.89 (m, 4H), 3.8 (s, 3H), 1.22-1.28 (m, 3H), 1.1 (s, 9H), 1.08 (s, 9H). LC/MS (ES+): (M+1), 281.2. Rf=0.8 (5% EtOAc/hexane). (Note: Alternatively, conventional heating might be adopted in which case NMP is the solvent of choice). washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL) After drying over anhydrous Na2SO4 the filtrate is concentrated The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)

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

Procedure: nBuLi (2.5 M in hexanes) (36 mmol) is mixed with TMEDA (36 mmol) at 0° C. in a dry round bottom flask for 10 minutes. A solution of triisopropyl-(2-methoxy-phenoxy)-silane (24 mmol) in 25 mL of dry THF is added to the above mixture. The mixture is warmed up to room temperature in 2 hours by removal of the ice bath. The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature. The mixture is stirred overnight. HCl (1 M) is added to the mixture to quench the reaction. The mixture is diluted with EtOAc (100 mL), washed with HCl (1 M) (2×100 mL) and brine (50 mL) and finally dried over anhydrous Na2SO4. Purification is accomplished by silica flash chromatography (5% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as a colorless oil which needs to be stored at low temperatures: 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 7.42 (dd, J1=7.7 Hz, J2=1.7 Hz, 1H), 7.67 (d, J1=8 Hz, J2=1.7 Hz, 1H), 7.04 (t, J=8.4 Hz, 1H), 3.96 (s, 3H), 1.26-1.35 (m, 3H), 1.13 (s, 9H), 1.12 (s, 9H). LC/MS (ES+): (M+1) 309.2. Rf=0.4 (5% EtOAc/hexane). The slightly yellow solution is then transferred to another dry flask containing dry 7.5 mL of DMF at room temperature HCl (1 M) is added to the mixture to quench the reaction washed with HCl (1 M) (2×100 mL) and brine (50 mL) finally dried over anhydrous Na2SO4 Purification

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Guaiacol (2-methoxy-phenol, 34.6 mmol) is mixed with TIPSCl (51.9 mmol) and imidazole (103.8 mmol) in a tube. The mixture is heated in the microwave oven at 180° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying over anhydrous Na2SO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield triisopropyl-(2-methoxy-phenoxy)-silane as a colorless oil. Yield: 69%. 1H NMR (400 MHz, CDCl3) δ 6.8-6.89 (m, 4H), 3.8 (s, 3H), 1.22-1.28 (m, 3H), 1.1 (s, 9H), 1.08 (s, 9H). LC/MS (ES+): (M+1), 281.2. Rf=0.8 (5% EtOAc/hexane). (Note: Alternatively, conventional heating might be adopted in which case NMP is the solvent of choice). washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL) After drying over anhydrous Na2SO4 the filtrate is concentrated The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)