methyl 10-bromodecanoate

反応条件: temp:0.00; pressure:0.00; stir:

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: A mixture of methyl 10-bromodecanoate (1.5 g, 0.006 mol), 4-chlorobenzenesulphonamide (3.44 g, 0.018 mol), potassium carbonate (6.2 g, 0.045 mol) and dimethylformamide (50 ml) was heated at 100°-120° C. for 3 hours. After cooling, the inorganic material was removed by filtration. The filtrate was evaporated to dryness and the residue was extracted with dichloromethane. The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) and the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°) to give the title compound (0.9 g, m.p. 68°-70° C.). was heated at 100°-120° C. for 3 hours After cooling the inorganic material was removed by filtration The filtrate was evaporated to dryness the residue was extracted with dichloromethane The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°)

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Hydroxy-isophthalic acid di-tert-butyl ester (90 mg, 0.3 mmol) was dissolved in dry acetone (5 ml), K2CO3 (90 mg, 0.65 mmol) and methyl 10-bromodecanoate (0.075 ml, 0.3 mmol) was added. The mixture was heated to reflux. The heating caused dissolution of the K2CO3. After a while, a precipitate was formed. Reflux (50° C.) was continued over night. More K2CO3 (30 mg, 0.2 mmol) and methyl 10-bromodecanoate (0.025 ml, 0.1 mmol) was added. The mixture was refluxed at 50° C. over night. To the dry reaction mixture EtOAc and water was added. After extraction, the organic layer was washed with water and brine, dried (Na2SO4) and concentrated to give the crude title compound as a clear oil. The mixture was heated to reflux After a while, a precipitate was formed was continued over night The mixture was refluxed at 50° C. over night was added After extraction the organic layer was washed with water and brine dried (Na2SO4) concentrated

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

実験手順: A mixture of methyl-10bromodecanoate (5.22 g), triphenylphosphine (7.74 g) and sodium iodide (0.3 g) in acetonitrile (50 ml) was refluxed for 24 hours. was refluxed for 24 hours

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

実験手順: A solution of 10-bromodecanoic acid (5 g) in methanol (60 ml) and concentrated sulphuric acid (3 drops) was refluxed for 20 hours.

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

実験手順: A solution of 10-bromodecanoic acid (5 g) in methanol (60 ml) and concentrated sulphuric acid (3 drops) was refluxed for 20 hours.

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

実験手順: 4-Mercaptobenzoic acid (2.0 g, 13 mmol) was placed in THF (25 ml). DIEA (3.7 g, 28.5 mmol) was added followed by a solution of methyl 10-bromodecanoate (3.44 g, 13 mmol) in THF (10 ml). After 1 h the solvent was removed under vacuum to yield a slurry, which was stored at rt for 3 days. AcOEt (100 ml) and 1 N HCl (50 ml) were added, but the precipitate did not dissolve very well. Sat. NaCl was added and then methanol in order to aid phase separation. The aqueous phase was removed, and DCM was added to the organic phase, but the precipitates still did not dissolve. The organic phase was concentrated under vacuum and dried with toluene by adding and evaporating twice. Drying under vacuum yielded a white solid (4.4 g, quantitative yield). After 1 h the solvent was removed under vacuum to yield a slurry, which the precipitate did not dissolve very well phase separation The aqueous phase was removed DCM was added to the organic phase the precipitates still did not dissolve The organic phase was concentrated under vacuum dried with toluene by adding evaporating twice Drying under vacuum

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

実験手順: 4-Mercaptobenzoic acid (2.0 g, 13 mmol) was placed in THF (25 ml). DIEA (3.7 g, 28.5 mmol) was added followed by a solution of methyl 10-bromodecanoate (3.44 g, 13 mmol) in THF (10 ml). After 1 h the solvent was removed under vacuum to yield a slurry, which was stored at rt for 3 days. AcOEt (100 ml) and 1 N HCl (50 ml) were added, but the precipitate did not dissolve very well. Sat. NaCl was added and then methanol in order to aid phase separation. The aqueous phase was removed, and DCM was added to the organic phase, but the precipitates still did not dissolve. The organic phase was concentrated under vacuum and dried with toluene by adding and evaporating twice. Drying under vacuum yielded a white solid (4.4 g, quantitative yield). After 1 h the solvent was removed under vacuum to yield a slurry, which the precipitate did not dissolve very well phase separation The aqueous phase was removed DCM was added to the organic phase the precipitates still did not dissolve The organic phase was concentrated under vacuum dried with toluene by adding evaporating twice Drying under vacuum

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

実験手順: 4-Mercaptobenzoic acid (2.0 g, 13 mmol) was placed in THF (25 ml). DIEA (3.7 g, 28.5 mmol) was added followed by a solution of methyl 10-bromodecanoate (3.44 g, 13 mmol) in THF (10 ml). After 1 h the solvent was removed under vacuum to yield a slurry, which was stored at rt for 3 days. AcOEt (100 ml) and 1 N HCl (50 ml) were added, but the precipitate did not dissolve very well. Sat. NaCl was added and then methanol in order to aid phase separation. The aqueous phase was removed, and DCM was added to the organic phase, but the precipitates still did not dissolve. The organic phase was concentrated under vacuum and dried with toluene by adding and evaporating twice. Drying under vacuum yielded a white solid (4.4 g, quantitative yield). After 1 h the solvent was removed under vacuum to yield a slurry, which the precipitate did not dissolve very well phase separation The aqueous phase was removed DCM was added to the organic phase the precipitates still did not dissolve The organic phase was concentrated under vacuum dried with toluene by adding evaporating twice Drying under vacuum

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

実験手順: A mixture of methyl 10-bromodecanoate (1.5 g, 0.006 mol), 4-chlorobenzenesulphonamide (3.44 g, 0.018 mol), potassium carbonate (6.2 g, 0.045 mol) and dimethylformamide (50 ml) was heated at 100°-120° C. for 3 hours. After cooling, the inorganic material was removed by filtration. The filtrate was evaporated to dryness and the residue was extracted with dichloromethane. The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) and the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°) to give the title compound (0.9 g, m.p. 68°-70° C.). was heated at 100°-120° C. for 3 hours After cooling the inorganic material was removed by filtration The filtrate was evaporated to dryness the residue was extracted with dichloromethane The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°)

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

実験手順: A mixture of methyl 10-bromodecanoate (1.5 g, 0.006 mol), 4-chlorobenzenesulphonamide (3.44 g, 0.018 mol), potassium carbonate (6.2 g, 0.045 mol) and dimethylformamide (50 ml) was heated at 100°-120° C. for 3 hours. After cooling, the inorganic material was removed by filtration. The filtrate was evaporated to dryness and the residue was extracted with dichloromethane. The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) and the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°) to give the title compound (0.9 g, m.p. 68°-70° C.). was heated at 100°-120° C. for 3 hours After cooling the inorganic material was removed by filtration The filtrate was evaporated to dryness the residue was extracted with dichloromethane The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°)