Reaktion #1857552

Reaktionsgleichung

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

DMSO

→

title compound

Ausbeute 99.2%

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

Ausbeute 99.2%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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