反应详情

温度

0 °C

22-Hydroxy-docosanoic acid was synthesized according to Mori et al., Liebigs Ann. Chem., (1991), 253-257. Briefly, under N2 atmosphere 6.6 g Docos-21-enoic acid ethyl ester and 30 ml THF were combined and cooled down to 0° C. Then 0.5 eq. (9 ml) borane/THF complex was added dropwise and the mixture was allowed to stir for 2 hours at room temperature. After the addition of 1.2 ml H2O the suspension was again cooled down to 0° C. and 15 ml 3M NaOH and 2 ml 35% H2O2 were added. The mixture was stirred for one hour at 50° C. Then the temperature was brought to room temperature and the pH was adjusted to pH 2-3 with 2N HCl. The solid was fritted, washed with H2O, codistilled three times with CHCl3 and recrystallized from CHCl3. After a further treatment with NaOH (3M in H2O) in THF at 50° C. over 1.5 days the pH was again adjusted to pH 2-3 and the crude product was fritted, washed with H2O and codistilled two times with CHCl3. The product was characterized by thin layer chromatography and 1H-NMR.

1. additionThen 0.5 eq. (9 ml) borane/THF complex was added dropwise
2. additionwere added
3. stirringThe mixture was stirred for one hour at 50° C
4. customwas brought to room temperature
5. washwashed with H2O
6. customrecrystallized from CHCl3
7. waitAfter a further treatment with NaOH (3M in H2O) in THF at 50° C. over 1.5 days the pH was again adjusted to pH 2-3
8. washwashed with H2O