chlorocyclopentane

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

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

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chloropyrimidin-5-ol (1 g, 7.66 mmol), chlorocyclopentane (2.39 mL, 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6% yield) as a white solid. MS (LC/MS) R.T.=2.32; [M+H]+=199.23. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over sodium sulfate concentrated in vacuo The residue was purified by column chromatography (0-25% ethyl acetate/hexanes)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chloropyrimidin-5-ol (1 g, 7.66 mmol), chlorocyclopentane (2.39 mL, 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6% yield) as a white solid. MS (LC/MS) R.T.=2.32; [M+H]+=199.23. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over sodium sulfate concentrated in vacuo The residue was purified by column chromatography (0-25% ethyl acetate/hexanes)

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

Procedure: The reaction was carried out under the same condition as in Example 3, except that the same amount of t-butyl chloride was used as the hydrogen chloride source. A mixture of cyclopentyl chloride and t-butyl chloride having the mixing ratio of 1:2 was reacted with metallic silicon at 280° C. to give 30.1 g of reaction products. The reaction products contained 6.2 g (39.1%) of cyclopentyldichlorosilane and 0.3 g (1.6%) of cyclopentyltrichlorosilane. There were not starting materials unreacted. As other by-products, 3.7 g (58.4%) of cyclopentene, 2.9 g of trichlorosilane and unconfirmed materials were obtained. was reacted with metallic silicon at 280° C. to give 30.1 g of reaction products

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

Procedure: Absolute ethanol (600 ml) was added with metal sodium (13.8 g) and butylmercaptan (64.8 g). A solution of 2-chlorocyclopentane (71.1 g) in absolute ethanol (600 ml) was added to the mixture and then was allowed to stand overnight at a low temperature. The ethanol was removed from the mixture, and the residue was dissolved in ether. The resulting solution was neutralized with aqueous acetic acid solution, the solvent was evaporated, and the resultant was then subjected to distillation, thereby giving 2-buthylthiocyclopentanone (90 g). The ethanol was removed from the mixture the residue was dissolved in ether the solvent was evaporated the resultant was then subjected to distillation giving 2-buthylthiocyclopentanone (90 g)

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

Procedure: Absolute ethanol (600 ml) was added with metal sodium (13.8 g) and butylmercaptan (64.8 g). A solution of 2-chlorocyclopentane (71.1 g) in absolute ethanol (600 ml) was added to the mixture and then was allowed to stand overnight at a low temperature. The ethanol was removed from the mixture, and the residue was dissolved in ether. The resulting solution was neutralized with aqueous acetic acid solution, the solvent was evaporated, and the resultant was then subjected to distillation, thereby giving 2-buthylthiocyclopentanone (90 g). The ethanol was removed from the mixture the residue was dissolved in ether the solvent was evaporated the resultant was then subjected to distillation giving 2-buthylthiocyclopentanone (90 g)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chloropyrimidin-5-ol (1 g, 7.66 mmol), chlorocyclopentane (2.39 mL, 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6% yield) as a white solid. MS (LC/MS) R.T.=2.32; [M+H]+=199.23. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over sodium sulfate concentrated in vacuo The residue was purified by column chromatography (0-25% ethyl acetate/hexanes)

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 200-ml four-necked flask sufficiently purged with nitrogen was equipped with a stirrer, a thermometer and a reflux condenser. 5.5 g (40 mmol) of trichlorophosphine and 40.0 ml of tetrahydrofuran were weighed in the flask. A cyclopentylmagnesium chloride solution was added dropwise to the flask at an internal temperature of 10-20° C. over a period of 3 hours, wherein the solution had been previously prepared from 13.8 g (132 mmol) of cyclopentyl chloride and 3.2 g (132 mmol) of metallic magnesium in 49 g of tetrahydrofuran. The mixture was stirred at 20-30° C. for 2 hours. Gas chromatography analysis confirmed the disappearance of trichlorophosphine. After the completion of the reaction, 61 ml of toluene was added, and 11.8 g (6 mmol) of 5% sulfuric acid was added dropwise to dissolve the magnesium salt, followed by separation. The organic phase was washed with 11.8 ml of water, and a solution of tricyclopentylphosphine was obtained. A 200-ml four-necked flask sufficiently purged with nitrogen was equipped with a stirrer was added followed by separation The organic phase was washed with 11.8 ml of water

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 200-ml four-necked flask sufficiently purged with nitrogen was equipped with a stirrer, a thermometer and a reflux condenser. 5.5 g (40 mmol) of trichlorophosphine and 40.0 ml of tetrahydrofuran were weighed in the flask. A cyclopentylmagnesium chloride solution was added dropwise to the flask at an internal temperature of 10-20° C. over a period of 3 hours, wherein the solution had been previously prepared from 13.8 g (132 mmol) of cyclopentyl chloride and 3.2 g (132 mmol) of metallic magnesium in 49 g of tetrahydrofuran. The mixture was stirred at 20-30° C. for 2 hours. Gas chromatography analysis confirmed the disappearance of trichlorophosphine. After the completion of the reaction, 61 ml of toluene was added, and 11.8 g (6 mmol) of 5% sulfuric acid was added dropwise to dissolve the magnesium salt, followed by separation. The organic phase was washed with 11.8 ml of water, and a solution of tricyclopentylphosphine was obtained. A 200-ml four-necked flask sufficiently purged with nitrogen was equipped with a stirrer was added followed by separation The organic phase was washed with 11.8 ml of water

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