1-chloropentane

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:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A three neck 300 ml flask fitted with a reflux condenser, thermometer and dropping funnel was charged with 18.52 grams (0.15 moles) of commercially available 2-ethoxy benzylcyanide in 50 ml of dimethyl sulfoxide (DMSO). To the reaction was added 17.6 grams (0.165 moles, 1.1 ec.) of 1-chloropentane. While stirring at room temperature, 13.2 grams (0.165 moles) of 50% NaOH in 20 ml of DMSO was added over 20 minutes. A slight exotherm occurred and the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) indicated the reaction was 92% complete. The reaction was stirred for an additional 3 hours, then water was added followed by 200 ml of ether. After washing with acid and brine, the solvent was concentrated and gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm) and gave 15.82 grams (47.7% yield) of product. A three neck 300 ml flask fitted with a reflux condenser the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) The reaction was stirred for an additional 3 hours After washing with acid and brine the solvent was concentrated gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm)

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: To a solution of freshly prepared sodium ethoxide (ca. 17 mmole) in ethanol (12 ml) was added with stirring 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (4.0 g, 17 mmole). After one hour, 1-chloropentane (4 ml, ca. 34 mmole) was added and the reaction mixture was stirred at room temperature for 20 hours. Water was added, and the mixture was extracted with diethyl ether. The ether layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel and recrystallization from pentane gave the title compound, m.p. 54°-55°. the mixture was extracted with diethyl ether The ether layer was dried over magnesium sulfate filtered concentrated in vacuo to an oil Chromatography on silica gel and recrystallization from pentane

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

Procedure: 10.7 g (0.1 mol) of n-pentyl chloride was dripped into a mixture of 2.5 g (0.1 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 300 ml THF solution of 45 g (0.1 mol) of 4-(trans-4-(2-(4-chloro-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-chlorobiphenyl to obtain 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-chlorobiphenyl. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 31.3 g (yield 69.9%) of the trans isomer. to obtain a Grignard's reagent

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

Procedure: A three neck 300 ml flask fitted with a reflux condenser, thermometer and dropping funnel was charged with 18.52 grams (0.15 moles) of commercially available 2-ethoxy benzylcyanide in 50 ml of dimethyl sulfoxide (DMSO). To the reaction was added 17.6 grams (0.165 moles, 1.1 ec.) of 1-chloropentane. While stirring at room temperature, 13.2 grams (0.165 moles) of 50% NaOH in 20 ml of DMSO was added over 20 minutes. A slight exotherm occurred and the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) indicated the reaction was 92% complete. The reaction was stirred for an additional 3 hours, then water was added followed by 200 ml of ether. After washing with acid and brine, the solvent was concentrated and gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm) and gave 15.82 grams (47.7% yield) of product. A three neck 300 ml flask fitted with a reflux condenser the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) The reaction was stirred for an additional 3 hours After washing with acid and brine the solvent was concentrated gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm)

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

Procedure: A three neck 300 ml flask fitted with a reflux condenser, thermometer and dropping funnel was charged with 18.52 grams (0.15 moles) of commercially available 2-ethoxy benzylcyanide in 50 ml of dimethyl sulfoxide (DMSO). To the reaction was added 17.6 grams (0.165 moles, 1.1 ec.) of 1-chloropentane. While stirring at room temperature, 13.2 grams (0.165 moles) of 50% NaOH in 20 ml of DMSO was added over 20 minutes. A slight exotherm occurred and the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) indicated the reaction was 92% complete. The reaction was stirred for an additional 3 hours, then water was added followed by 200 ml of ether. After washing with acid and brine, the solvent was concentrated and gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm) and gave 15.82 grams (47.7% yield) of product. A three neck 300 ml flask fitted with a reflux condenser the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) The reaction was stirred for an additional 3 hours After washing with acid and brine the solvent was concentrated gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm)