Reaktion #6091

Reaktionsgleichung

4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside

sodium methylate

→

expected product

Ausbeute 89.7%

4-cyanophenyl 1,5-dithio-β-D-xylopyranoside

Ausbeute 89.7%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONhas completely dissolved (2 hours)
2. 2
   workup.ADDITIONis then neutralized by the addition of Amberlite® IR 120 H+ resin
3. 3
   SonstigeThe methanol is evaporated off under reduced pressure
4. 4
   Sonstigethe crude product obtained
5. 5
   Sonstigeis recrystallized from an ethanol/water mixture (65/25 v/v)

Vorschrift

Under a nitrogen atmosphere, 8.5 g (21.10-3 mol) of 4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 1a) are suspended in 100 ml of methanol, and 2 ml of sodium methylate (8% w/v of Na in methanol) are then added. The reaction medium is stirred at room temperature until the starting material has completely dissolved (2 hours) and is then neutralized by the addition of Amberlite® IR 120 H+ resin. The methanol is evaporated off under reduced pressure; the crude product obtained is recrystallized from an ethanol/water mixture (65/25 v/v) to give 5.3 g (yield: 89.7%) of the expected product.

Quelle