Reacción #1857552

Ecuación de reacción

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

DMSO

→

title compound

Rendimiento 99.2%

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

Rendimiento 99.2%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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]+).

Fuente