反应 #2200585

反应方程式

water

(2R,3S)-2-methyl-3-benzyloxybutanol

Et3N

ether

→

(2S,3S)-2-methyl-3-benzyloxybutyraldehyde

溶剂

DMSO

反应条件

后处理

1. 1
   workup.WAITat room temperature for 2 hours
2. 2
   萃取The aqueous layer was extracted with ether
3. 3
   洗涤The combined ether extracts were washed with 1M HCl, waters saturated NaHCO3, brine, and they
4. 4
   干燥were dried over Na2SO4
5. 5
   其他evaporated in order

实验过程

The Py.SO3 complex (4.09 g, 25.67 mmol, 6.0 eq.) was added in portions at 0° C. to a solution of (2R,3S)-2-methyl-3-benzyloxybutanol (13) (830 mg, 4.28 mmol) and Et3N (2.86 g, 3.93 ml, 28.25 mmol, 6.6 eq.) in DMSO (14 ml). The reaction mixture is stirred at 0° C. for 3.5 hours, and then at room temperature for 2 hours, and then it was divided between water and ether. The aqueous layer was extracted with ether. The combined ether extracts were washed with 1M HCl, waters saturated NaHCO3, brine, and they were dried over Na2SO4 and evaporated in order to obtain crude (2S,3S)-2-methyl-3-benzyloxybutyraldehyde which was used directly for the next reaction without purification. 1H NMR (250 MHz, CDCl3) δ 9.73 (d, J=2.4 Hz, 1H); 4.63 (d, J=11.7 Hz, 1H); 4.44 (d, J=11.7 Hz, 1H); 3.81 (quintuplet, J=6.4 Hz, 1H); 2.57 (quintuplet-d, J=7.0; 2.4 Hz, 1H); 1.25 (d, J=6.2 Hz, 3H); 1.09 (d, J=7.1 Hz, 3H).

来源