反应详情

温度

-78 °C

3.17 g (25.04 mmol) of oxalyl chloride is introduced into 83 ml of dichloromethane and cooled to −78° C. At this temperature, 3.9 g (50.08 mmol) of dimethyl sulfoxide, dissolved in 10 ml of dichloromethane, is added in drops. After five minutes of stirring, 7.15 g (21.38 mmol) of 4-(3-isopropyl-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-pentane-1,2-diol, dissolved in 21.4 ml of dichloromethane, is added. Then, the reaction mixture is stirred for two hours at this low temperature. 10.8 g (106.9 mmol) of triethylamine is carefully added in drops, and the batch is then stirred vigorously at room temperature for one hour. After water is added and after stirring is done for another ten minutes, it is extracted twice with dichloromethane. The combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine. After the solvent is dried and spun off, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 5.93 g (83.44%) of the desired aldehyde is ultimately obtained.

1. additionis added in drops
2. additionis added
3. stirringThen, the reaction mixture is stirred for two hours at this low temperature
4. stirringthe batch is then stirred vigorously at room temperature for one hour
5. stirringafter stirring
6. waitis done for another ten minutes
7. extractionit is extracted twice with dichloromethane
8. washThe combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine
9. customAfter the solvent is dried
10. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)