3-trimethylsilylpropan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a similar manner to Example 1, 25 g (0.19 mol) of 3-(trimethylsilyl)propanol, 2.5 g of KOH and 25 g of DMSO were reacted at 80° C. with acetylene. 3-(Trimethylsilyl)propyl vinyl ether was obtained in 96% yield.

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An ethereal solution of magnesium iodide was prepared by adding 4.85 g (19 mmol) of iodine to 0.46 g (19 mmol) of magnesium in suspension in 40 ml of dry ether. 28 ml of this solution was added to a solution containing the crude 3-(trimethylsilyl)-1-propanol, methanesulfonate in 10 ml of ether. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ether and water, the organic phase was separated and further washed with aqueous sodium thiosulfate. After evaporation of the solvent, 1.6 g of (3-iodopropyl)trimethysilane was obtained as a colorless liquid. partitioned between ether and water the organic phase was separated further washed with aqueous sodium thiosulfate After evaporation of the solvent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methanesulfonylchloride (0.73 ml, 9 mmol) was added dropwise to a solution of 3-(trimethylsilyl)-1-propanol (1.2 ml, 7.56 mmol) cooled at 0° C. in 20 ml of dichloromethane. After 45 minutes stirring, the reaction mixture was partitioned between water and dichloromethane, the organic phase was separated, the solvent was evaporated under reduced pressure to afford the expected 3-(trimethylsilyl)-1-propanol, methanesulfonate in crude quantitative yield. the reaction mixture was partitioned between water and dichloromethane the organic phase was separated the solvent was evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An ethereal solution of magnesium iodide was prepared by adding 4.85 g (19 mmol) of iodine to 0.46 g (19 mmol) of magnesium in suspension in 40 ml of dry ether. 28 ml of this solution was added to a solution containing the crude 3-(trimethylsilyl)-1-propanol, methanesulfonate in 10 ml of ether. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ether and water, the organic phase was separated and further washed with aqueous sodium thiosulfate. After evaporation of the solvent, 1.6 g of (3-iodopropyl)trimethysilane was obtained as a colorless liquid. partitioned between ether and water the organic phase was separated further washed with aqueous sodium thiosulfate After evaporation of the solvent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methanesulfonylchloride (0.73 ml, 9 mmol) was added dropwise to a solution of 3-(trimethylsilyl)-1-propanol (1.2 ml, 7.56 mmol) cooled at 0° C. in 20 ml of dichloromethane. After 45 minutes stirring, the reaction mixture was partitioned between water and dichloromethane, the organic phase was separated, the solvent was evaporated under reduced pressure to afford the expected 3-(trimethylsilyl)-1-propanol, methanesulfonate in crude quantitative yield. the reaction mixture was partitioned between water and dichloromethane the organic phase was separated the solvent was evaporated under reduced pressure

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 12.5 mL of water was added 8.73 g (0.0873 mole) of chromium trioxide which was mixed until all solid had dissolved. This solution was immersed in an ice/water bath, and 13.4 g (7.3 mL, 0.137 mole) of concentrated sulfuric acid (18M) was added cautiously. This was followed by the addition of 25 mL of water. The solution was then cooled to 0°-5° C. and added to a stirred solution of 16.5 g (0.125 mole) of 4,4-dimethyl-4-silapentanol in 800 mL of acetone which had been cooled to 0°-10° C. in an ice/water bath. During the addition the temperature was maintained at 20° C., and stirring was continued for three hours after the addition was complete. At the conclusion of this period sodium bisulfite was added to the reaction mixture in small portions until the brown color of chromic acid had disappeared from the upper layer. The two layers were separated, and the dense, green lower layer was extracted with 200 mL of petroleum ether. The layers were separated, and the upper layer was added to the upper layer which had been previously separated. This caused two phases to form. The layers were separated, and the lower layer was added to the lower layer from the reaction mixture. The combined lower layers were extracted three times with 200 mL of petroleum ether. The extracts were combined with the previously separated petroleum ether extract, and this mixture was successively washed twice with a saturated aqueous solution of sodium chloride, twice with a saturated aqueous solution of sodium bicarbonate, and finally with a saturated aqueous solution of sodium chloride. After being dried over anhydrous magnesium sulfate, the solvent was evaporated from the combined extracts under reduced pressure, leaving 4,4-dimethyl-4-silapentanoic acid as a residue. The NMR spectrum was consistent with the proposed structure. This is the method described in Organic Synthesis, Vol. V, p 866. was mixed until all solid had dissolved This solution was immersed in an ice/water bath The solution was then cooled to 0°-5° C. had been cooled to 0°-10° C. in an ice/water bath During the addition the temperature after the addition The two layers were separated the dense, green lower layer was extracted with 200 mL of petroleum ether The layers were separated the upper layer was added to the upper layer which had been previously separated to form The layers were separated the lower layer was added to the lower layer from the reaction mixture were extracted three times with 200 mL of petroleum ether extract this mixture was successively washed twice with a saturated aqueous solution of sodium chloride, twice with a saturated aqueous solution of sodium bicarbonate After being dried over anhydrous magnesium sulfate the solvent was evaporated from the combined extracts under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid and 3-trimethylsilylpropanol according to the procedure of Example 30 as a white foam (HCl salt); 1H NMR (CDCl3) δ 0.01 (s, 18H), 0.46 (m, 4H), 1.33 (d, J=6.3 Hz, 3H), 1.70 (m, 4H), 2.80 (m, 1H), 3.18 (m, 2H), 3.46(m 2H), 4.24(t, J=7.0 Hz, 4H), 5.47 (bd, J=9.7 Hz, I H), 5.70 (bs, 1H), 6.80 (m, 3H), 7.25 (m, 2H), 7.43 (s, 1H), 8.70 (bs, 1H), 10.10 (bs, 1H); IR (KBr): 1765 cm-1 (C=O); MS (ES) m/z 650 (MH+); [α]D25 -22° (c, 1.0, CHCl3). Anal. Calcd. for C32H48ClNO7Si2 ·HCl: C, 55.96; H, 7.04; N, 2.04 Cl, 10.32; Si, 8.18. Found: C, 55.82; H, 7.21; N, 1.87; Cl, 10.22; Si, 7.76.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a similar manner to Example 1, 25 g (0.19 mol) of 3-(trimethylsilyl)propanol, 2.5 g of KOH and 25 g of DMSO were reacted at 80° C. with acetylene. 3-(Trimethylsilyl)propyl vinyl ether was obtained in 96% yield.