2-chlorocyclopentan-1-one

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: To a mixture of 4-benzyloxyphenol (5 g, 25 mmol), potassium iodide (125 mg), and potassium carbonate (4.48 g, 32.5 mmol) in 2-butanone (30 ml) was added 2-chlorocyclopentanone (5.9 g, 50 mmol). The mixture was heated at reflux for 5 h, filtered and concentrated in vacuo. The residue was dissolved in diethyl ether and washed successively with 10% aqueous sodium hydroxide, water and brine. After drying over magnesium sulfate, solvents were removed in vacuo and the residue subjected to flash chromatography on silica gel eluting with 30% diethyl ether in hexanes to afford the title compound as a pale orange solid (2.4 g). The mixture was heated at reflux for 5 h filtered concentrated in vacuo The residue was dissolved in diethyl ether washed successively with 10% aqueous sodium hydroxide, water and brine After drying over magnesium sulfate, solvents were removed in vacuo

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chlorocyclopentanone (5.00 g, 39.5 mmol) and thiourea (3.00 g, 39.5 mmol) was heated at 80° C. for 3-4 minutes. After cooling to room temperature, the mixture was triturated with ethanol and the solid was collected by filtration to afford the title compound. MS (ESI) m/z 141 (M+H)+. After cooling to room temperature the mixture was triturated with ethanol the solid was collected by filtration

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chlorocyclopentanone (5.00 g, 39.5 mmol) and thiourea (3.00 g, 39.5 mmol) was heated at 80° C. for 3-4 minutes. After cooling to room temperature, the mixture was triturated with ethanol and the solid was collected by filtration to afford the title compound. MS (ESI) m/z 141 (M+H)+. After cooling to room temperature the mixture was triturated with ethanol the solid was collected by filtration

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

Procedure: 17.7 g (0.15 mol) of 2-chlorocyclopentanone and 41.4 g (0.3 mol) of potassium carbonate are added to a solution of 20 g (0.1 mol) of 3-hydroxy-4-methoxy-bromobenzene in 300 ml of absolute DMF and the mixture is stirred at RT for 12 h. After filtering off the solids, the filtrate is concentrated, the residue is taken up in 500 ml of ethyl ether and the solution is extracted by shaking with 3×200 ml of distilled water. Column chromatography affords 21.1 g of the title compound as a brown oil [TLC (petroleum ether/ethyl acetate 6:4) Rf =0.47]. After filtering off the solids the filtrate is concentrated the solution is extracted by shaking with 3×200 ml of distilled water

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

Procedure: 17.7 g (0.15 mol) of 2-chlorocyclopentanone and 41.4 g (0.3 mol) of potassium carbonate are added to a solution of 20 g (0.1 mol) of 3-hydroxy-4-methoxy-bromobenzene in 300 ml of absolute DMF and the mixture is stirred at RT for 12 h. After filtering off the solids, the filtrate is concentrated, the residue is taken up in 500 ml of ethyl ether and the solution is extracted by shaking with 3×200 ml of distilled water. Column chromatography affords 21.1 g of the title compound as a brown oil [TLC (petroleum ether/ethyl acetate 6:4) Rf =0.47]. After filtering off the solids the filtrate is concentrated the solution is extracted by shaking with 3×200 ml of distilled water

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-2-methoxyphenol (6.31 g), α-chlorocyclopentanone (6.9 ml), potassium carbonate (9.57 g), and DMF (63 ml) was stirred at 90° C. for 2 hours. α-Chlorocyclopentanone (14 ml) was further added to the mixture, followed by stirring at 90° C. for one hour. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic, layer was washed with a 1N aqueous solution of sodium hydroxide and then with a saturated saline, and dried over sodium sulfate. The solvent, was distilled off, and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give Compound IIl-a (11.8 g, 99%) as an oily substance. by stirring at 90° C. for one hour for cooling followed by extraction with ether The organic, layer was washed with a 1N aqueous solution of sodium hydroxide with a saturated saline, and dried over sodium sulfate The solvent, was distilled off the residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give Compound IIl-a (11.8 g, 99%) as an oily substance

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-2-methoxyphenol (120.0 g), 2-chloro-1-cyclopentanone (100.0 g), potassium carbonate (163.3 g), and DMF (1.2 l) was stirred at 70° C. for 3 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give Compound IIc-a (141.43 g, 83.9%) as a pale-yellow oily substance. for cooling followed by extraction with ethyl acetate The organic layer was washed with a saturated saline dried over anhydrous magnesium sulfate the solvent was distilled off The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give Compound IIc-a (141.43 g, 83.9%) as a pale-yellow oily substance

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chlorocyclopentanone (5.0 g, 40 mmol) and thiourea (3.0 g, 40 mmol) was heated at 70° C. for 3 hours. After cooling, the solid was triturated with ethanol and collected by filtration to afford the title compound. MS (ESI) m/z 141 (M+H)+. After cooling the solid was triturated with ethanol collected by filtration