反应详情

温度

0 °C

A solution of 4-methoxybenzyl 2-(acetoxymethyl)-5-(hydroxymethyl)benzoate (480.4 mg, 1.40 mmol) obtained from Example 1-(9) in dichloromethane (10 ml) was cooled to 0° C., and then tetrazole (195.4 mg, 2.79 mmol) and bis(allyloxy)(diisopropylamino)phosphine (Tetrahedron Lett., 30, 4219 (1989); 444.9 mg, 1.82 mmol) were added thereto with stirring, followed by stirring the mixture at the same temperature for 15 minutes. After the reaction mixture was warmed to room temperature and stirred for 1 hour, methanol (12 drops) was added thereto. The mixture was stirred for 5 minutes and then cooled to 0° C., and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 0.54 g, 4.8 mmol) was added thereto, then the mixture was warmed to room temperature and stirred for 15 minutes. A saturated aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium thiosulfate were added thereto, and the mixture was stirred for 10 minutes and partitioned between ethyl acetate and water. The obtained organic layers were combined and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (25 g) column (eluent; ethyl acetate:hexane=1:2˜1:1) to afford the title compound (598.3 mg, 85% yield) as a colorless oil.

1. stirringby stirring the mixture at the same temperature for 15 minutes
2. temperatureAfter the reaction mixture was warmed to room temperature
3. stirringstirred for 1 hour
4. stirringThe mixture was stirred for 5 minutes
5. temperaturecooled to 0° C.
6. temperaturethe mixture was warmed to room temperature
7. stirringstirred for 15 minutes
8. stirringthe mixture was stirred for 10 minutes
9. custompartitioned between ethyl acetate and water
10. distillationthe solvent was distilled off under reduced pressure
11. customto give an oily residue