2-octylpropane-1,3-diol

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

Procedure: Quantities: compound from Example 9 (48.3 g, 0.26 mol), 4-bromobenzaldehyde (46.5 g, 0.25 mol) and 4-toluenesulphonic acid (150 mg). The experimental procedure was as described in Example 11.

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

Procedure: Quantities: compound from Example 9 (48.3 g, 0.26 mol), 4-bromobenzaldehyde (46.5 g, 0.25 mol) and 4-toluenesulphonic acid (150 mg). The experimental procedure was as described in Example 11.

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

Procedure: Quantities: compound from Example 9 (48.3 g, 0.26 mol), 4-bromobenzaldehyde (46.5 g, 0.25 mol) and 4-toluenesulphonic acid (150 mg). The experimental procedure was as described in Example 11.

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

Procedure: Quantities: compound from Example 4 (76.5 g, 0.28 mol) and lithium aluminum hydride (23 g, 0.6 mol). The experimental procedure was as described in Example 6. The product was obtained as a colourless solid. The product was obtained as a colourless solid

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

Procedure: A mixture of 2-n-octylpropane-1,3-diol (5.64 g, 0.03 m), 4-hydroxybenzaldehyde (3.66 g, 0.03 m), benzene (60 ml) and a catalytic amount of 4-toluenesulfonic acid was azeotropically refluxed until no more water was collected (about 16 hours). The solvent was evaporated and the residue was crystallized from 50% aqueous ethanol to yield p-(5-n-octyl-1,3-dioxan-2-yl)phenol (4 g, 48%) mp 96°-97° C. was collected (about 16 hours) The solvent was evaporated the residue was crystallized from 50% aqueous ethanol

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

Procedure: Borane methyl sulfide (BMS) complex (80 g, 1 m) was added dropwise to a mixture of diethyl-n-octylmalonate (90 g, 0.33) and tolune (400 ml) with stirring at room temperature. Stirring was continued for an additional hour. The mixture was refluxed gently for 10 hours, cooled to 20° C., and then poured slowly into ice-cold methanol (400 ml) with stirring and left to stand overnight. The solvent was stripped off and the residue was stirred with 10% hydrochloric acid solution (400 ml) overnight. The resulting mixture was extracted with chloroform (2×70 ml) and washed with water until neutral to litmus. The solvent was evaporated and the residue was vacuum distilled to yield 2-n-octylpropane-1,3-diol (25.5 g, 41%) bp 135°-140° C./0.5-0.8 mm. Stirring was continued for an additional hour The mixture was refluxed gently for 10 hours cooled to 20° C. with stirring left The resulting mixture was extracted with chloroform (2×70 ml) washed with water until neutral to litmus The solvent was evaporated distilled

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

Procedure: 2.20 g (6.68 mmol) of 2-fluoro-3-formyl-6-(4-octyloxyphenyl)pyridine, 1.26 g (6.68 mmol) of 2-octylpropane-1,3-diol, 0.02g (0.10mmol) of p-toluenesulfonic acid and 3.00 g of sodium sulfate are stirred in 100 ml of toluene at room temperature for 68 hours. 0.14 ml (1.00 mmol) of triethylamine is then added, sodium sulfate is filtered off, the filtrate is concentrated, and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile, giving 1.40 g of 2-fluoro-3-(5-octyl-1,3-dioxane-2-yl)-6-(4-octyloxyphenyl)pyridine. ##STR63## sodium sulfate is filtered off the filtrate is concentrated the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and by recrystallization from acetonitrile

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

Procedure: 1.00 g (3.00 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid (prepared as described in Example 10), 0.56 g (3.00 mmol) of 2-octylpropane-1,3-diol and 1.50 g of sodium sulfate in 30 ml of tetrahydrofuran are stirred at room temperature for 48 hours. Sodium sulfate is then filtered off, the filtrate is concentrated, and the residue is recrystallized from hexane, giving 1.24 g of 2-fluoro-3-(5-octyl-1,3-dioxaborinan-2-yl)-6-(4-octyloxyphenyl)pyridine. ##STR61## Sodium sulfate is then filtered off the filtrate is concentrated the residue is recrystallized from hexane

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

Procedure: In a 500-ml egg-plant type flask were put 32.3 g of 2-octyl-1,3-propanediol, 22.5 g of p-cyanobenzaldehyde, 0.11 g of p-toluenesulfonic acid monohydrate and 300 ml of benzene, and the mixture was heated. The generated water was removed by azeotropy with benzene. Then, benzene was distilled away, and the residue was neutralized with aqueous saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane, and the extract was washed with water and then dried over anhydrous sodium sulfate. Dichloromethane was distilled away to give a solid which was then recrystallized from isooctane to give 37.7 g of colorless crystals. In a 500-ml egg-plant type flask were put The generated water was removed by azeotropy with benzene Then, benzene was distilled away The mixture was extracted with dichloromethane the extract was washed with water dried over anhydrous sodium sulfate Dichloromethane was distilled away to give a solid which was then recrystallized from isooctane

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

Procedure: 250 ml of ether and 19.0 of lithium aluminum hydride were put in a 1-liter four-necked flask, and a solution obtained by dissolving 72.1 g of the thus prepared diethyl octylmalonate in 50 ml of ether was put therein dropwise at such a rate that ether is gently refluxed. After the dropwise addition, the mixture was refluxed with heating for 3 hours, and after allowing it to cool, a mixture of water-THF was added to decompose excess lithium aluminum hydride. The resultant solid was removed by filtration, and the filtrate was washed with saturated saline and dried over anhydrous sodium sulfate. The crude crystal obtained by distilling away the solvents was recrystallized from isooctane to give 32.4 g of colorless crystals. Yield 65%. a solution obtained After the dropwise addition the mixture was refluxed with heating for 3 hours to cool was added The resultant solid was removed by filtration the filtrate was washed with saturated saline dried over anhydrous sodium sulfate The crude crystal obtained by distilling away the solvents was recrystallized from isooctane