反応 #2200585

反応方程式

water

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

Et3N

ether

→

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

溶媒

DMSO

反応条件

後処理

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

実験手順

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).

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