6-fluoro-2,2-dimethyl-3H-chromen-4-one

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

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

Procedure: A solution of 6-fluoro-2,2-dimethyl-chroman-4-one (EP 193493; 1 equiv.) in ethanol (0.24 M) was treated with copper chromite (0.6 equiv.). The reaction was heated to 200° C. for 6 hours at 3000 psi of hydrogen gas. The reaction was filtered and concentrated to a solid. The crude material was recrystallized form hot hexanes to give the title compound. MS found 198 [M+H]+ The reaction was filtered concentrated to a solid The crude material was recrystallized form hot hexanes

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

Procedure: By heating 10 mmol of 6-fluoro-2,2-dimethyl-4-chromanone with 12 mmol of hydroxylamine hydrochloride in 5 ml of methanol and 5 ml of pyridine for 2 hours to 80° C., after distilling off the solvent and precipitating with water, 6-fluoro-2,2-dimethyl-4-chromanone oxime is obtained; m.p. 108-110° C. after distilling off the solvent precipitating with water

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

Procedure: By heating 10 mmol of 6-fluoro-2,2-dimethyl-4-chromanone with 12 mmol of hydroxylamine hydrochloride in 5 ml of methanol and 5 ml of pyridine for 2 hours to 80° C., after distilling off the solvent and precipitating with water, 6-fluoro-2,2-dimethyl-4-chromanone oxime is obtained; m.p. 108-110° C. after distilling off the solvent precipitating with water

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

Procedure: A solution of 6-fluoro-2,2-dimethyl-chroman-4-one (EP 193493; 1 equiv.) in ethanol (0.24 M) was treated with copper chromite (0.6 equiv.). The reaction was heated to 200° C. for 6 hours at 3000 psi of hydrogen gas. The reaction was filtered and concentrated to a solid. The crude material was recrystallized form hot hexanes to give the title compound. MS found 198 [M+H]+ The reaction was filtered concentrated to a solid The crude material was recrystallized form hot hexanes

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

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

Procedure: In a 500 mL round-bottomed flask was added 1-(5-fluoro-2-hydroxyphenyl)ethanone (20.0 g, 130 mmol, Aldrich Chemical), propan-2-one (19.0 mL, 260 mmol), and pyrrolidine (21.5 mL, 260 mmol) in methanol (150 mL) to give a orange solution. The reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was poured into EtOAc (200 mL) and washed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to provide an orange residue which was purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes) to provide the title compound (14.2 g, 73.1 mmol, 56%) as a white solid. MS (DCI/NH3) m/z 208 (M+NH4)+. to give a orange solution washed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL) The organic portion was dried (Na2SO4) filtered concentrated to provide an orange residue which was purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes)

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

Procedure: In a 500 mL round-bottomed flask was added 1-(5-fluoro-2-hydroxyphenyl)ethanone (20.0 g, 130 mmol, Aldrich Chemical), propan-2-one (19.0 mL, 260 mmol), and pyrrolidine (21.5 mL, 260 mmol) in methanol (150 mL) to give a orange solution. The reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was poured into EtOAc (200 mL) and washed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to provide an orange residue which was purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes) to provide the title compound (14.2 g, 73.1 mmol, 56%) as a white solid. MS (DCI/NH3) m/z 208 (M+NH4)+. to give a orange solution washed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL) The organic portion was dried (Na2SO4) filtered concentrated to provide an orange residue which was purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes)

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

Procedure: By heating 10 mmol of 6-fluoro-2,2-dimethyl-4-chromanone with 12 mmol of hydroxylamine hydrochloride in 5 ml of methanol and 5 ml of pyridine for 2 hours to 80° C., after distilling off the solvent and precipitating with water, 6-fluoro-2,2-dimethyl-4-chromanone oxime is obtained; m.p. 108-110° C. after distilling off the solvent precipitating with water

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

Procedure: A solution of 6-fluoro-2,2-dimethyl-chroman-4-one (EP 193493; 1 equiv.) in ethanol (0.24 M) was treated with copper chromite (0.6 equiv.). The reaction was heated to 200° C. for 6 hours at 3000 psi of hydrogen gas. The reaction was filtered and concentrated to a solid. The crude material was recrystallized form hot hexanes to give the title compound. MS found 198 [M+H]+ The reaction was filtered concentrated to a solid The crude material was recrystallized form hot hexanes