tetradecane-1-thiol

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 mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C. is heated on a steam bath overnight then refluxed for one-half hour The mixture is then cooled extracted with ether-water The ether layer is washed with water and salt water dried over sodium sulfate filtered The filtrate is evaporated to dryness the remaining solid is recrystallized from hexane and from methanol

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

Procedure: A mixture of 18.6 g (0.090 mole) of 5-bromo-2-thiophenecarboxylic acid, 25.0 g (0.109 mole) of 1-tetradecanethiol and 500 ml of dried dimethyl acetamide is stirred at room temperature after which 10.8 g (0.200 mole) of sodium methoxide is added. The mixture is heated and the methanol formed is allowed to distill off. The mixture is refluxed for 24 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with 10% aqueous hydrochloric acid, filtered, and the precipitate washed with water and dried. The solid obtained is crystallized from the methanol then recrystallized from hexane to give 5-(tetradecylthio)-2 -thiophene carboxylic acid, M.P. 106°-108° C. is added The mixture is heated to distill off The mixture is refluxed for 24 hours after which the mixture is cooled poured into a water-ice mixture filtered the precipitate washed with water dried The solid obtained is crystallized from the methanol then recrystallized from hexane

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

Procedure: 460 μl of a 30% solution of sodium methoxide in methanol were added to a solution of 665 μl of tetradecanethiol in a 5 ml methanol/2 ml THF mixture, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then 0.47 g of methyl 7-chloro-3-thia-5-heptynoate in 5 ml of methanol was added, under an inert atmosphere. The mixture was maintained under stirring for 8 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The wax thus obtained was chromatographed on a silica gel column (CH2Cl2) providing 1.05 g of methyl 3,8-dithia-5-docosynoate in the form of an oil. (Quantitative yield). The mixture was maintained The mixture was maintained under stirring for 8 hours at room temperature extracted 3 times with ethyl ether The combined organic phases were washed 3 times with water with a saturated aqueous solution of NaCl before being dried (Na2SO4) filtered concentrated under vacuum in a rotary evaporator The wax thus obtained was chromatographed on a silica gel column (CH2Cl2)

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

Procedure: A mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C. is heated on a steam bath overnight then refluxed for one-half hour The mixture is then cooled extracted with ether-water The ether layer is washed with water and salt water dried over sodium sulfate filtered The filtrate is evaporated to dryness the remaining solid is recrystallized from hexane and from methanol

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

Procedure: A mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C. is heated on a steam bath overnight then refluxed for one-half hour The mixture is then cooled extracted with ether-water The ether layer is washed with water and salt water dried over sodium sulfate filtered The filtrate is evaporated to dryness the remaining solid is recrystallized from hexane and from methanol

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

Procedure: This compound was prepared in the same manner as for the title compound of Example 2, except that 2-DAT was replaced with tetradecanethiol.

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

Procedure: This compound was prepared in the same manner as for the title compound of Example 2, except that 2-DAT was replaced with tetradecanethiol.

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

Procedure: A mixture of 18.6 g (0.090 mole) of 5-bromo-2-thiophenecarboxylic acid, 25.0 g (0.109 mole) of 1-tetradecanethiol and 500 ml of dried dimethyl acetamide is stirred at room temperature after which 10.8 g (0.200 mole) of sodium methoxide is added. The mixture is heated and the methanol formed is allowed to distill off. The mixture is refluxed for 24 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with 10% aqueous hydrochloric acid, filtered, and the precipitate washed with water and dried. The solid obtained is crystallized from the methanol then recrystallized from hexane to give 5-(tetradecylthio)-2 -thiophene carboxylic acid, M.P. 106°-108° C. is added The mixture is heated to distill off The mixture is refluxed for 24 hours after which the mixture is cooled poured into a water-ice mixture filtered the precipitate washed with water dried The solid obtained is crystallized from the methanol then recrystallized from hexane