反応 #1857552

反応方程式

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

DMSO

→

title compound

収率 99.2%

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

収率 99.2%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他followed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2
2. 2
   その他The 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
   その他The phases were separated
5. 5
   洗浄the organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL)
6. 6
   乾燥The solution was dried over magnesium sulfate (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

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]+).

出典