1-iodo-3,3-dimethylbutane

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:

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 the 2,5-dihydroxybenzaldehyde in DMF was added K2CO3 at room temperature and the mixture was stirred for 10 min. To this solution 1-iodo-3,3-dimethylbutane was added. After stirring at 70° C. for 4 h, the solvent was removed under reduced pressure and reaction mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by column chromatography to give desired product in 65% yield. 1H NMR: 0.97 (s, 9H), 1.73 (t, 2H, J=7.2 Hz), 4.05 (t, 2H, J=7.2 Hz), 6.88 (d, 1H, J=9.2 Hz), 7.09 (dd, 1H, J=9.2, 3.2 Hz), 7.35 (d, 1H, J=3.2 Hz), 10.39 (s, 1H) After stirring at 70° C. for 4 h the solvent was removed under reduced pressure and reaction mixture was diluted with ethyl acetate After washing with water the organic layer was dried over Na2SO4 concentrated under vacuum The crude product was purified by column chromatography

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

実験手順: 1-(3-Hydroxy-5-methoxyphenyl)ethanone (O3.033; 1.12 g) and 1-iodo-3,3-dimethylbutane (1.57 g) were dissolved in DMF, and sodium hydride (194 mg) was added. After stirring at RT for 2 h, the DMF was drawn off. The residue was taken up in EA, washed with water, dried, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min). 850 mg of the title compound were obtained. washed with water dried filtered concentrated The residue was purified silica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min)

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

実験手順: To a solution of lithium bis(trimethylsilyl)amide in (154.48 g, 0.923 mol) in tetrahydrofuran (350 mL) was added 2-phenyl propionic acid (50.0 g, 0.333 mol) over 27 minutes maintaining the temperature below 25° C. Following a THF rinse (35 mL), the solution was heated to 50° C. for 23 minutes. The solution was then cooled below 25° C. and 3,3-dimethyl-1-iodobutane (110.3 g, 0.416 mol) was added. The reaction mixture was heated to 60° C. for 31 h, then was cooled to RT, and concentrated to a thick oil. Water (500 mL) was added and the solution was cooled to 10-15° C. and the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g). The product was extracted with ethyl acetate (440 mL) and the organic layer was washed with 10% NaCl. The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil and used in the resolution. maintaining the temperature below 25° C rinse (35 mL) The solution was then cooled below 25° C. The reaction mixture was heated to 60° C. for 31 h was cooled to RT concentrated to a thick oil Water (500 mL) was added the solution was cooled to 10-15° C. the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g) The product was extracted with ethyl acetate (440 mL) the organic layer was washed with 10% NaCl The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil

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

実験手順: To a solution of lithium bis(trimethylsilyl)amide in (154.48 g, 0.923 mol) in tetrahydrofuran (350 mL) was added 2-phenyl propionic acid (50.0 g, 0.333 mol) over 27 minutes maintaining the temperature below 25° C. Following a THF rinse (35 mL), the solution was heated to 50° C. for 23 minutes. The solution was then cooled below 25° C. and 3,3-dimethyl-1-iodobutane (110.3 g, 0.416 mol) was added. The reaction mixture was heated to 60° C. for 31 h, then was cooled to RT, and concentrated to a thick oil. Water (500 mL) was added and the solution was cooled to 10-15° C. and the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g). The product was extracted with ethyl acetate (440 mL) and the organic layer was washed with 10% NaCl. The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil and used in the resolution. maintaining the temperature below 25° C rinse (35 mL) The solution was then cooled below 25° C. The reaction mixture was heated to 60° C. for 31 h was cooled to RT concentrated to a thick oil Water (500 mL) was added the solution was cooled to 10-15° C. the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g) The product was extracted with ethyl acetate (440 mL) the organic layer was washed with 10% NaCl The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil

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:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of lithium bis(trimethylsilyl)amide in (154.48 g, 0.923 mol) in tetrahydrofuran (350 mL) was added 2-phenyl propionic acid (50.0 g, 0.333 mol) over 27 minutes maintaining the temperature below 25° C. Following a THF rinse (35 mL), the solution was heated to 50° C. for 23 minutes. The solution was then cooled below 25° C. and 3,3-dimethyl-1-iodobutane (110.3 g, 0.416 mol) was added. The reaction mixture was heated to 60° C. for 31 h, then was cooled to RT, and concentrated to a thick oil. Water (500 mL) was added and the solution was cooled to 10-15° C. and the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g). The product was extracted with ethyl acetate (440 mL) and the organic layer was washed with 10% NaCl. The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil and used in the resolution. maintaining the temperature below 25° C rinse (35 mL) The solution was then cooled below 25° C. The reaction mixture was heated to 60° C. for 31 h was cooled to RT concentrated to a thick oil Water (500 mL) was added the solution was cooled to 10-15° C. the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g) The product was extracted with ethyl acetate (440 mL) the organic layer was washed with 10% NaCl The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil

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

実験手順: To a solution of lithium bis(trimethylsilyl)amide in (154.48 g, 0.923 mol) in tetrahydrofuran (350 mL) was added 2-phenyl propionic acid (50.0 g, 0.333 mol) over 27 minutes maintaining the temperature below 25° C. Following a THF rinse (35 mL), the solution was heated to 50° C. for 23 minutes. The solution was then cooled below 25° C. and 3,3-dimethyl-1-iodobutane (110.3 g, 0.416 mol) was added. The reaction mixture was heated to 60° C. for 31 h, then was cooled to RT, and concentrated to a thick oil. Water (500 mL) was added and the solution was cooled to 10-15° C. and the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g). The product was extracted with ethyl acetate (440 mL) and the organic layer was washed with 10% NaCl. The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil and used in the resolution. maintaining the temperature below 25° C rinse (35 mL) The solution was then cooled below 25° C. The reaction mixture was heated to 60° C. for 31 h was cooled to RT concentrated to a thick oil Water (500 mL) was added the solution was cooled to 10-15° C. the pH was adjusted to <2 by the addition of 6 N HCl (75.59 g) The product was extracted with ethyl acetate (440 mL) the organic layer was washed with 10% NaCl The crude ethyl acetate solution (assayed for 66.8 g of 49-1, 85.6%) was concentrated to a thick oil