Реакция #1857552

Уравнение реакции

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

DMSO

→

title compound

Выход 99.2%

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

Выход 99.2%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Другоеfollowed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2
2. 2
   ДругоеThe 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
   ДругоеThe phases were separated
5. 5
   Промывкаthe organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL)
6. 6
   СушкаThe solution was dried over magnesium sulfate (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated

Методика

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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