Реакция #8282

Уравнение реакции

methanol dichloromethane

ethyl pent-4-enoate

4-methylmorpholine N-oxide

tetrahydrofuran

→

title compound

Выход 96.0%

4,5-Dihydroxy-pentanoic acid ethyl ester

Выход 96.0%

Растворители

water

Условия реакции

Обработка

1. 1
   КонцентрированиеThe mixture is concentrated in vacuo
2. 2
   Другоеthe residue chromatographed on SiO2 (2% methanol/ethyl acetate)

Методика

A solution of ethyl pent-4-enoate (11.7 g, 91.3 mmol) in tetrahydrofuran (420 mL) and water (40 mL) is treated with osmium tetroxide (1.0 g, 4.2 mmol) and 4-methylmorpholine N-oxide (32.5 mL, 50% in water) at room temperature and stired for 3 h, at which time no more starting material is detectable by TLC (SiO2, 2% methanol/dichloromethane, Rf=0.40). The mixture is concentrated in vacuo and the residue chromatographed on SiO2 (2% methanol/ethyl acetate) to afford the title compound 14.37 g (96%) as a colorless oil.

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