methyl 12-bromododecanoate

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

実験手順: 12-Bromododecanoic acid methyl ester (5.65 g, 19.3 mmol) was dissolved in acetone (50 ml). Sodium iodide (14.4 g, 96 mmol) was added and the reaction was refluxed under nitrogen for 20 h. The sample was concentrated under vacuum. Water (100 ml) was added, and the mixture was extracted with AcOEt (2×100 ml). The organic extracts were pooled and washed with water plus a small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4, and concentrated to yield a light yellow oil (6.37 g, 97%). the reaction was refluxed under nitrogen for 20 h The sample was concentrated under vacuum Water (100 ml) was added the mixture was extracted with AcOEt (2×100 ml) washed with water a small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4 concentrated

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

実験手順: 12-Bromododecanoic acid methyl ester (5.65 g, 19.3 mmol) was dissolved in acetone (50 ml). Sodium iodide (14.4 g, 96 mmol) was added and the reaction was refluxed under nitrogen for 20 h. The sample was concentrated under vacuum. Water (100 ml) was added, and the mixture was extracted with AcOEt (2×100 ml). The organic extracts were pooled and washed with water plus a small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4, and concentrated to yield a light yellow oil (6.37 g, 97%). the reaction was refluxed under nitrogen for 20 h The sample was concentrated under vacuum Water (100 ml) was added the mixture was extracted with AcOEt (2×100 ml) washed with water a small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4 concentrated

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12-Bromododecanoic acid (10 g, 35.8 mmol) was stirred with methanol (60 ml) and Toluene (180 ml). Trimethyl orthoformate (38 g, 358 mmol) and Amberlyst A-15 (ca. 1 g) were added. The reaction was mixed for 16 h. At some point the heating unit failed, So the reaction cooled from 70° C. to rt. The solution was heated to 70° C. and mixed for 24 h. TLC (2:1 heptane/AcOEt) indicated the reaction was incomplete. Trimethyl orthoformate (38 g, 358 mmol) and Amberlyst A-15 (1.4 g) were added, and the solution was stirred at 70° C. for 16 h. The sample was concentrated under vacuum to yield a brown oil (9.87 g). Vacuum distillation at 0.09 torr yielded two fractions of colorless oil (109-117° C., 6.95 g; 117-129° C., 1.17 g). These were combined and dissolved in AcOEt (100 ml) and washed with Sat. NaHCO3 (2×40 ml), dried over MgSO4 and concentrated under vacuum. The oil was dissolved in 20:1 AcOEt/TEA (10 ml) and added to a bed of silica (3 cm×7.5 cm dia). The column was eluted with AcOEt/TEA 20:1 (200 ml), and the filtrate was concentrated under vacuum. The oil was dissolved in AcOEt (100 ml) and washed with 1 N HCl (2×40 ml), dried over MgSO4 and concentrated under vacuum to yield a colorless oil (7.52 g, 72% yield). The reaction was mixed for 16 h cooled from 70° C. to rt mixed for 24 h The sample was concentrated under vacuum