반응 #1857552

반응 방정식

(2R,3S)-2-benzyl-3((4-methoxybenzyl)oxy)butan-1-ol

DMSO

→

title compound

수율 99.2%

(2S,3S)-2-benzyl-3((4-methoxybenzyl)oxy)butanal

수율 99.2%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타followed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2
2. 2
   기타The reaction was removed from the cold bath
3. 3
   workup.ADDITIONThe reaction was diluted with ice cold 0.5 N HCl (100 mL) and EtOAc (150 mL)
4. 4
   기타The phases were separated
5. 5
   세척the organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL)
6. 6
   건조The solution was dried over magnesium sulfate (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a solution of (2R,3S)-2-benzyl-3((4-methoxybenzyl)oxy)butan-1-ol (5.38 g, 17.91 mmol) in CH2Cl2 (90 mL) in a nitrogen flushed 250 mL round bottomed flask was added DMSO (17.9 mL, 25.24 mmol) and TEA (12.5 mL, 90 mmol) via syringe followed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2. The reaction was removed from the cold bath and allowed to warm to room temperature, and stirred for 2 h. The reaction was diluted with ice cold 0.5 N HCl (100 mL) and EtOAc (150 mL). The phases were separated and the organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL). The solution was dried over magnesium sulfate (MgSO4), filtered, and concentrated to afford the title compound (5.3 g, 96%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 9.78 (d, J=2.8 Hz, 1H), 7.29-7.09 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 4.56 (d, J=11.3 Hz, 1H), 4.34 (d, J=11.3 Hz, 1H), 3.82 (s, 3H), 3.03 (dd, J=14.0, 8.2 Hz, 1H), 2.87 (dd, J=14.0, 6.4 Hz, 2H), 2.78-2.55 (m, 1H), 1.29 (d, J=6.4 Hz, 3H); ESIMS m/z 321.3 ([M+Na]+).

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