(2-bromo-3-methylphenyl)-(2,3-dihydrofuran-5-yl)methanone

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

実験手順: A solution of (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone (0.80 g, 2.99 mmol) (mass approximate, based on ˜8 mg/mL Et2O solution) was treated with 500 mL EtOAc and concentrated to ˜100 mL twice. The resulting solution was placed under N2 atmosphere, treated with 5% Pt/C, and then placed under a balloon of H2. Reaction mixture was allowed to stir overnight, then filtered through plug of celite and the filter agent was further washed with 100 mL EtOAc. The solution was concentrated in vacuo and the crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane to afford (2-bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone. concentrated to ˜100 mL twice treated with 5% Pt/C Reaction mixture filtered through plug of celite the filter agent was further washed with 100 mL EtOAc The solution was concentrated in vacuo the crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane

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

実験手順: A solution of (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone (0.80 g, 2.99 mmol) (mass approximate, based on ˜8 mg/mL Et2O solution) was treated with 500 mL EtOAc and concentrated to ˜100 mL twice. The resulting solution was placed under N2 atmosphere, treated with 5% Pt/C, and then placed under a balloon of H2. Reaction mixture was allowed to stir overnight, then filtered through plug of celite and the filter agent was further washed with 100 mL EtOAc. The solution was concentrated in vacuo and the crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane to afford (2-bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone. concentrated to ˜100 mL twice treated with 5% Pt/C Reaction mixture filtered through plug of celite the filter agent was further washed with 100 mL EtOAc The solution was concentrated in vacuo the crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,3-dihydrofuran (0.70 mL, 9.25 mmol) in THF (9.0 mL) under inert atmosphere was cooled to −78° C. A solution of n-butyllithium, 1.7 M in pentanes (5.98 mL, 10.17 mmol), was added dropwise over 10 min. The reaction was maintained at that temperature for 30 min, and allowed to warm to 0° C. for 30 min. It was cooled back down to −78° C. and then added via cannula to a solution of (2-bromo-3-methylphenyl)(morpholino)methanone (2.02 g, 7.12 mmol) in Et2O (17.92 mL), also at −78° C. The solution was stirred at that temperature for 10 min and then allowed to warm to 0° C. The mixture was partitioned between Et2O and water and the organics were washed with water and brine. The solution was dried over Na2SO4 and concentrated. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of Et2O in hexane, to provide (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone as a colorless oil. This oil was immediately re-dissolved in Et2O and placed under nitrogen before storing in the freezer for further use. The reaction was maintained at that temperature for 30 min It was cooled back down to −78° C. to warm to 0° C The mixture was partitioned between Et2O and water the organics were washed with water and brine The solution was dried over Na2SO4 concentrated The crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of Et2O in hexane

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

実験手順: A solution of (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone (0.80 g, 2.99 mmol) (mass approximate, based on ˜8 mg/mL Et2O solution) was treated with 500 mL EtOAc and concentrated to ˜100 mL twice. The resulting solution was placed under N2 atmosphere, treated with 5% Pt/C, and then placed under a balloon of H2. Reaction mixture was allowed to stir overnight, then filtered through plug of celite and the filter agent was further washed with 100 mL EtOAc. The solution was concentrated in vacuo and the crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane to afford (2-bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone. concentrated to ˜100 mL twice treated with 5% Pt/C Reaction mixture filtered through plug of celite the filter agent was further washed with 100 mL EtOAc The solution was concentrated in vacuo the crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,3-dihydrofuran (0.70 mL, 9.25 mmol) in THF (9.0 mL) under inert atmosphere was cooled to −78° C. A solution of n-butyllithium, 1.7 M in pentanes (5.98 mL, 10.17 mmol), was added dropwise over 10 min. The reaction was maintained at that temperature for 30 min, and allowed to warm to 0° C. for 30 min. It was cooled back down to −78° C. and then added via cannula to a solution of (2-bromo-3-methylphenyl)(morpholino)methanone (2.02 g, 7.12 mmol) in Et2O (17.92 mL), also at −78° C. The solution was stirred at that temperature for 10 min and then allowed to warm to 0° C. The mixture was partitioned between Et2O and water and the organics were washed with water and brine. The solution was dried over Na2SO4 and concentrated. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of Et2O in hexane, to provide (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone as a colorless oil. This oil was immediately re-dissolved in Et2O and placed under nitrogen before storing in the freezer for further use. The reaction was maintained at that temperature for 30 min It was cooled back down to −78° C. to warm to 0° C The mixture was partitioned between Et2O and water the organics were washed with water and brine The solution was dried over Na2SO4 concentrated The crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of Et2O in hexane