1-phenylpent-4-yn-1-ol

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: To a solution of oxalyl chloride (7.0 mL, 76.6 mmol) in methylene chloride (200 mL) under argon atmosphere at -78° C. was added dropwise dimethylsulfoxide (11.9 mL, 152 mmol). After stirring for 15 minutes 1-hydroxy-1-phenylpent-4-yne (11.14 g, 69.6 mmol) in methylene chloride (20 mL) was added dropwise. After stirring at -78° C. for 1 hour triethylamine (48 mL, 340 mmol) was added and the orange reaction mixture was allowed to warm to room temperature. Water (100 mL) was added, the layers separated, and the organic extract was washed with 1% hydrochloric acid solution (4×100 mL), saturated sodium bicarbonate solution, brine, and dried (MgSO4). Evaporation of solvent under reduced pressure gave a solid which was recrystallized from petroleum ether to afford 5.25 g product. The mother liquors were distilled by Kugelrohr (80° C., 0.1 mm Hg) to give an additional 8.3 g (75 %) of product. 1H NMR (CDCl3) δ: 1.99 (t, J=2.69 Hz, 1H), 2.63 (t, J=7.21 Hz, 1H), 2.64 (t, J=6.17 Hz, 1H), 3.25 (t, J=6.23 Hz, 1H), 3.26 (t, J=7.20 Hz, 1H), 7.44-7.58 (m, 3H), 7.96-7.99 (m, 2H) ppm. was added dropwise was added the layers separated the organic extract was washed with 1% hydrochloric acid solution (4×100 mL), saturated sodium bicarbonate solution, brine dried (MgSO4) Evaporation of solvent under reduced pressure gave a solid which was recrystallized from petroleum ether

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

実験手順: To an ice-cold solution of 3.0M phenylmagnesium bromide (100 mL, 300 mmol) under argon atmosphere was added dropwise pent-4-yn-1-ol (10 g, 120 mmol) in diethyl ether (20 mL). After stirring for 3 hours the solution was slowly added to an ice-cold solution of dilute ammonium chloride. 6N Hydrochloric acid was added to break up the gel and the layers were separated. The aqueous extract was washed with diethyl ether (3×50 mL) and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which was Kugelrohr distilled to afford 11.1 g (58%) of the purified product. 1H NMR (CDCl3) δ: 1.82-1.95 (m, 2H), 1.98 (t, 1H), 2.20-2.35 (m, 2H), 2.40 (s, 1H), 4.80-4.85 (m, 1H), 7.30-7.38 (m, 5H) ppm. the layers were separated The aqueous extract was washed with diethyl ether (3×50 mL) the combined organic extracts were washed with brine dried (MgSO4) The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which distilled

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

実験手順: To an ice-cold solution of 3.0M phenylmagnesium bromide (100 mL, 300 mmol) under argon atmosphere was added dropwise pent-4-yn-1-ol (10 g, 120 mmol) in diethyl ether (20 mL). After stirring for 3 hours the solution was slowly added to an ice-cold solution of dilute ammonium chloride. 6N Hydrochloric acid was added to break up the gel and the layers were separated. The aqueous extract was washed with diethyl ether (3×50 mL) and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which was Kugelrohr distilled to afford 11.1 g (58%) of the purified product. 1H NMR (CDCl3) δ: 1.82-1.95 (m, 2H), 1.98 (t, 1H), 2.20-2.35 (m, 2H), 2.40 (s, 1H), 4.80-4.85 (m, 1H), 7.30-7.38 (m, 5H) ppm. the layers were separated The aqueous extract was washed with diethyl ether (3×50 mL) the combined organic extracts were washed with brine dried (MgSO4) The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which distilled

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

実験手順: To an ice-cold solution of 3.0M phenylmagnesium bromide (100 mL, 300 mmol) under argon atmosphere was added dropwise pent-4-yn-1-ol (10 g, 120 mmol) in diethyl ether (20 mL). After stirring for 3 hours the solution was slowly added to an ice-cold solution of dilute ammonium chloride. 6N Hydrochloric acid was added to break up the gel and the layers were separated. The aqueous extract was washed with diethyl ether (3×50 mL) and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which was Kugelrohr distilled to afford 11.1 g (58%) of the purified product. 1H NMR (CDCl3) δ: 1.82-1.95 (m, 2H), 1.98 (t, 1H), 2.20-2.35 (m, 2H), 2.40 (s, 1H), 4.80-4.85 (m, 1H), 7.30-7.38 (m, 5H) ppm. the layers were separated The aqueous extract was washed with diethyl ether (3×50 mL) the combined organic extracts were washed with brine dried (MgSO4) The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which distilled