trimethoxy(propyl)silane

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

Procedure: A 500 mL round bottomed flask was charged with magnesium powder (2.1 g, 86 mmol, Aldrich) and ether (250 mL, Aldrich). 2-Bromo-m-xylene (9.0 mL, 68 mmol, Aldrich) was added over a 25 minute period. The contents were refluxed overnight (18 hours). The brown solution was cooled to room temperature and propyl-trimethoxysilane (17.8 mL, 101 mmol) was added over 20 minutes. A white precipitate formed. The contents were stirred at room temperature overnight (18 hours). The reaction was poured into 0.2N aqueous HCI (500 mL), the layers were separated and the product extracted into ether (3×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (13.5 g crude). Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg) provided (2,6-dimethylphenyl)-propyl-dimethoxysilane (6.8 g, 28 mmol, 41% yield); C13H22SiO2 (Mw=238.40); 1H NMR (CDCl3) δ7.2 (t, 1H), 7.0 (d, 2H), 3.6 (s, 6H), 2.5 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ145.2, 131.0, 129.6, 128.0, 49.8, 23.4, 17.9, 16.7, 16.3; MS m/z (relative abundance) 238 (8), 195 (100), 165 (22), 133 (12), 119 (10), 105 (13), 91 (9), 59 (16). The contents were refluxed overnight (18 hours) A white precipitate formed The reaction was poured into 0.2N aqueous HCI (500 mL) the layers were separated the product extracted into ether (3×150 mL) The combined organic portions were dried (MgSO4) filtered the solvent removed via rotary evaporation (13.5 g crude) Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg)

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

Procedure: A 500 mL round bottomed flask was charged with hexane (200 mL, Aldrich) and bromo-2,4-dimethoxybenzene (12.2 g, 56.0 mmol, Aldrich). The contents were cooled to 0° C. and n-butyl lithium (34.7 mL of a 1.6M solution in hexanes, 55.5 mmol, Aldrich) was added over 15 minutes (white precipitate). The contents were stirred at room temperature for ninety (90) minutes. The solution was added, via cannula, into a 1000 mL round bottomed flask containing hexane (300 mL, Aldrich) and propyl-trimethoxysilane (9.8 mL, 56 mmol). The reaction was stirred at room temperature overnight (18 hours). Ethanol (10 mL, Aldrich) was added to quench residual base. The contents were poured into 0.2N HCl (250 mL). The layers were separated and the product extracted into ether (2×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (16.2 g crude). Distillation under reduced pressure (b.p. 115° C., 0.04 mm Hg) provided 2,4-dimethoxyphenyl-propyl-dimethoxysilane (9.13 g, 33.8 mmol, 61% yield); C13H22O4Si (Mw=270.40); 1H NMR (CDCl3) δ7.5 (d, 1H), 6.5 (m, 1H), 6.4 (d, 1H), 3.8 (s, 3H), 3.8 (s, 3H), 3.5 (s,6H), 1.4 (m, 2H), 0.9 (t, 3H), 0.8 (t, 2H); 13C NMR (CDCI3) δ165.8, 163.2, 137.6, 112.7, 104.6, 97.5, 55.0, 54.9, 50.4, 17.7, 16.2, 15.4; IR (capillary film) ν2950, 2836, 1596, 1571, 1460, 1299, 1206, 1154, 1089, 1036; MS m/z (relative abundance) 270 (11.1), 227 (45.6), 197 (100), 167 (24.4), 137 (10.9), 121 (22.6), 91 (9.9), 59 (18.4). The solution was added, via cannula, into a 1000 mL round bottomed flask to quench residual base The contents were poured into 0.2N HCl (250 mL) The layers were separated the product extracted into ether (2×150 mL) The combined organic portions were dried (MgSO4) filtered the solvent removed via rotary evaporation (16.2 g crude) Distillation under reduced pressure (b.p. 115° C., 0.04 mm Hg)

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

Procedure: A 500 mL round bottomed flask was charged with propyl-trimethoxysilane (19.3 mL, 1.10×10−1 mole, Hüls) and ether (250 mL, Aldrich). A pressure equalizing addition funnel was charged with phenylmagnesium bromide (33.3 mL of a 3M solution in ether, 99.9 mmol, Aldrich) and ether (50 mL). The contents of the addition funnel were added into the silane over a 20 minute period (exotherm). A white precipitate formed. The reaction was stirred for two hours at room temperature then poured into 0.2N HCl (300 mL). The layers were separated, the product extracted into ether (2×250 mL), dried (MgSO4), and filtered. The solvent was removed via rotary evaporation resulting in 23.5 grams of crude material. Distillation under reduced pressure (b.p. 71° C., 0.6 mm Hg) provided phenyl-propyl-dimethoxysilane (18.5 g, 88.0 mmol, 88% yield); C11H18SiO2 (mw=210.34); 1H NMR (CDCl3) δ7.7 (m, 2H), 7.4 (m, 3H), 3.6 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ134.3, 133.3, 130.1, 127.9, 50.6, 17.9, 16.3, 14.8; MS m/z (relative abundance) 210 (2), 167 (100), 137 (33), 107 (17), 91 (17), 59 (10). addition funnel A white precipitate formed The layers were separated the product extracted into ether (2×250 mL) dried (MgSO4) filtered The solvent was removed via rotary evaporation resulting in 23.5 grams of crude material Distillation under reduced pressure (b.p. 71° C., 0.6 mm Hg)

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

Procedure: A sol-gel formulation was prepared as follows. Glacial acetic acid (108.0 grams, 1.80 mol) was added dropwise to a previously prepared, stirred mixture of propyltrimethoxysilane (489.6 grams, 2.97 mol) and 3-glycidoxypropyltrimethoxysilane (122.4 grams, 0.518 mol), followed by the dropwise addition of 3-aminopropyltrimethoxysilane (49.6 grams, 0.277 mol). The acidified silanes were then hydrolyzed by the dropwise addition of excess water (312.0 grams, 17.3 mol). The following day, the clear solution was diluted to approximately 20 wt % solids by the dropwise addition of ethanol (1046 grams) and allowed to stir in a covered vessel for 1 week. DC-190 (16 grams) was subsequently added as a plasticizer, followed by the addition of lithium iodide (9.43 grams, 0.0704 mol) to provide a "sol-gel solution". A sol-gel formulation was prepared a previously prepared to stir in a covered vessel for 1 week DC-190 (16 grams) was subsequently added as a plasticizer to provide a "sol-gel solution"

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

Procedure: A 500 mL round bottomed flask was charged with magnesium powder (2.1 g, 86 mmol, Aldrich) and ether (250 mL, Aldrich). 2-Bromo-m-xylene (9.0 mL, 68 mmol, Aldrich) was added over a 25 minute period. The contents were refluxed overnight (18 hours). The brown solution was cooled to room temperature and propyl-trimethoxysilane (17.8 mL, 101 mmol) was added over 20 minutes. A white precipitate formed. The contents were stirred at room temperature overnight (18 hours). The reaction was poured into 0.2N aqueous HCl (500 mL), the layers were separated and the product extracted into ether (3×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (13.5 g crude). Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg) provided (2,6-dimethylphenyl)-propyl-dimethoxysilane (6.8 g, 28 mmol, 41% yield); C13H22SiO2 (Mw=238.40); 1H NMR (CDCl3) δ 7.2 (t, 1H), 7.0 (d, 2H), 3.6 (s, 6H), 2.5 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ 145.2, 131.0, 129.6, 128.0, 49.8, 23.4, 17.9, 16.7, 16.3; MS m/z (relative abundance) 238 (8), 195 (100), 165 (22), 133 (12), 119 (10), 105 (13), 91 (9), 59 (16). The contents were refluxed overnight (18 hours) A white precipitate formed the layers were separated the product extracted into ether (3×150 mL) The combined organic portions were dried (MgSO4) filtered the solvent removed via rotary evaporation (13.5 g crude) Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg)

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

Procedure: A 500 mL round bottomed flask was charged with hexane (200 mL, Aldrich) and bromo-2,4-dimethoxybenzene (12.2 g, 56.0 mmol, Aldrich). The contents were cooled to 0° C. and n-butyl lithium (34.7 mL of a 1.6M solution in hexanes, 55.5 mmol, Aldrich) was added over 15 minutes (white precipitate). The contents were stirred at room temperature for ninety (90) minutes. The solution was added, via cannula, into a 1000 mL round bottomed flask containing hexane (300 mL, Aldrich) and propyl-trimethoxysilane (9.8 mL, 56 mmol). The reaction was stirred at room temperature overnight (18 hours). Ethanol (10 mL, Aldrich) was added to quench residual base. The contents were poured into 0.2N HCl (250 mL). The layers were separated and the product extracted into ether (2×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (16.2 g crude). Distillation under reduced pressure (b.p. 115° C., 0.04 mm Hg) provided 2,4-dimethoxyphenyl-propyl-dimethoxysilane (9.13 g, 33.8 mmol, 61% yield); C13H22O4Si (Mw=270.40); 1H NMR (CDCl3) δ 7.5 (d, 1H), 6.5 (m, 1H), 6.4 (d, 1H), 3.8 (s, 3H), 3.8 (s, 3H), 3.5 (s, 6H), 1.4 (m, 2H), 0.9 (t, 3H), 0.8 (t, 2H); 13C NMR (CDCl3) δ 165.8, 163.2, 137.6, 112.7, 104.6, 97.5, 55.0, 54.9, 50.4, 17.7, 16.2, 15.4; IR (capillary film) ν 2950, 2836, 1596, 1571, 1460, 1299, 1206, 1154, 1089, 1036; MS m/z (relative abundance) 270 (11.1), 227 (45.6), 197 (100), 167 (24.4), 137 (10.9), 121 (22.6), 91 (9.9), 59 (18.4). The solution was added, via cannula, into a 1000 mL round bottomed flask to quench residual base The contents were poured into 0.2N HCl (250 mL) The layers were separated the product extracted into ether (2×150 mL) The combined organic portions were dried (MgSO4) filtered the solvent removed via rotary evaporation (16.2 g crude) Distillation under reduced pressure (b.p. 115° C., 0.04 mm Hg)

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

Procedure: A 500 mL round bottomed flask was charged with propyl-trimethoxysilane (19.3 mL, 1.10×10−1 mole, Hüls) and ether (250 mL, Aldrich). A pressure equalizing addition funnel was charged with phenylmagnesium bromide (33.3 mL of a 3M solution in ether, 99.9 mmol, Aldrich) and ether (50 mL). The contents of the addition funnel were added into the silane over a 20 minute period (exotherm). A white precipitate formed. The reaction was stirred for two hours at room temperature then poured into 0.2N HCl (300 mL). The layers were separated, the product extracted into ether (2×250 mL), dried (MgSO4), and filtered. The solvent was removed via rotary evaporation resulting in 23.5 grams of crude material. Distillation under reduced pressure (b.p. 71° C., 0.6 mm Hg) provided phenyl-propyl-dimethoxysilane (18.5 g, 88.0 mmol, 88% yield); C11H18SiO2 (mw=210.34); 1H NMR (CDCl3) δ 7.7 (m, 2H), 7.4 (m, 3H), 3.6 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ 134.3, 133.3, 130.1, 127.9, 50.6, 17.9, 16.3, 14.8; MS m/z (relative abundance) 210 (2), 167 (100), 137 (33), 107 (17), 91 (17), 59 (10). addition funnel A white precipitate formed The layers were separated the product extracted into ether (2×250 mL) dried (MgSO4) filtered The solvent was removed via rotary evaporation resulting in 23.5 grams of crude material Distillation under reduced pressure (b.p. 71° C., 0.6 mm Hg)

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

Procedure: 473.9 mg (19.5 mmols) of metal magnesium and 19.5 ml of diethyl ether were put into a 100-ml three-neck flask, to which were added a few drops of 1,2-dibromoethane. Then, 2.65 g (17.6 mmols) of neopentyl bromide was dropwise added thereto over a period of 50 minutes. This was ripened under reflux for 8 hours, and the disappearance of neopentyl bromide from it was confirmed. After restored to room temperature, the resulting solution was dropwise added to a solution of 2.60 g (15.8 mmols) of n-propyltrimethoxysilane in diethyl ether, and then refluxed for 14 hours. The disappearance of n-propyltrimethoxysilane from it was confirmed. 5 ml of methanol was added to this, and the resulting solution was filtered, dried, distilled and passed through a separation column to obtain 1.91 g of neopentyl-n-pentyldimethoxysilane. Its purity was 98.9%, and its yield was 59.5%. under reflux for 8 hours After restored to room temperature refluxed for 14 hours was filtered dried distilled passed through a separation column