cyclohexane-1,2-diol

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: Part A. A solution of 2-hydroxycyclohexanol (2.28 g, 0.02 mol), thiourea (1.52 g, 0.02 mol) and hexanol (30 ml), equipped with a column of 4Å sieves and a condenser, was heated to 160° for five hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature and was concentrated in vacuo to give a solid. The solid was triturated with ethyl ether (3×50 ml) to give 4,5,6,7-tetrahydrobenzimidazol-2-thione (0.6 g, 0.0039 mol) which was not purified but was taken on to the next step as a crude solid. was heated to 160° for five hours under a nitrogen atmosphere was concentrated in vacuo to give a solid The solid was triturated with ethyl ether (3×50 ml)

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: 25.3 gm (1.1 mol) of sodium were dissolved in 500 ml of ethanol under dry nitrogen. 116 gm (1 mol) of 1,2-cyclohexane-diol were added to the solution at room temperature. Then, the ethanol was completely removed under vacuum. 163 gm (1.2 mol) of the ethyl ester of 2-chloropropionic acid were added to the mono-sodium salt of 1,2-cyclohexane-diol so obtained, at 50° C., and the mixture was allowed to stand for 5 hours at 80° C. to react further. Then, the reaction mixture was decomposed with water and acidified with sulfuric acid. The organic phase was separated and the aqueous phase was extracted twice with ether. After combining the organic phases, these were washed neutral with water and sodium bicarbonate solution, dried over sodium sulfate and reduced under vacuum. The crude product obtained was distilled under high vacuum. 76 gm of 4-methyl-2,5-dioxabicyclo-[4,4,0]-decan-3-one were obtained with the following analytical data: Then, the ethanol was completely removed under vacuum so obtained, at 50° C. to react further The organic phase was separated the aqueous phase was extracted twice with ether these were washed neutral with water and sodium bicarbonate solution dried over sodium sulfate The crude product obtained was distilled under high vacuum

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

実験手順: In 30 ml of tetrahydrofuran was suspended 1.78 g of sodium hydride (60% in oil), to which 3 ml of a tetrahydrofuran solution containing 2.35 g of 1,2-cyclohexanediol (mixture of cis-form and trans-form) was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 10 minutes and then cooled to 0° C., to which 7 ml of a tetrahydrofuran solution containing 3 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by further stirring at 0° C. for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.6 g of 4-chloro-6-(2-hydroxycyclohexyloxy)pyrimidine. was slowly added dropwise The mixture was stirred at room temperature for 10 minutes was slowly added dropwise by further stirring at 0° C. for 3 hours extracted three times with ethyl acetate washed with brine dried over anhydrous magnesium sulfate concentrated

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

実験手順: In 30 ml of tetrahydrofuran was suspended 1.78 g of sodium hydride (60% in oil), to which 3 ml of a tetrahydrofuran solution containing 2.35 g of 1,2-cyclohexanediol (mixture of cis-form and trans-form) was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 10 minutes and then cooled to 0° C., to which 7 ml of a tetrahydrofuran solution containing 3 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by further stirring at 0° C. for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.6 g of 4-chloro-6-(2-hydroxycyclohexyloxy)pyrimidine. was slowly added dropwise The mixture was stirred at room temperature for 10 minutes was slowly added dropwise by further stirring at 0° C. for 3 hours extracted three times with ethyl acetate washed with brine dried over anhydrous magnesium sulfate concentrated

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

実験手順: Part A. A solution of 2-hydroxycyclohexanol (2.28 g, 0.02 mol), thiourea (1.52 g, 0.02 mol) and hexanol (30 ml), equipped with a column of 4Å sieves and a condenser, was heated to 160° for five hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature and was concentrated in vacuo to give a solid. The solid was triturated with ethyl ether (3×50 ml) to give 4,5,6,7-tetrahydrobenzimidazol-2-thione (0.6 g, 0.0039 mol) which was not purified but was taken on to the next step as a crude solid. was heated to 160° for five hours under a nitrogen atmosphere was concentrated in vacuo to give a solid The solid was triturated with ethyl ether (3×50 ml)