Réaction #353194

Équation de réaction

mannitol

NaHCO3

Sodium periodate

→

title product

Isopropylidene-glyceraldehyde

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was decanted off
2. 2
   workup.STIRRINGthe remaining solid was stirred in CH2Cl2
3. 3
   Filtrationfiltered
4. 4
   Autreto remove the excess solid
5. 5
   Concentrationconcentrated in vacuo
6. 6
   workup.DISTILLATIONThe resulting oil was distilled at reduced pressure

Mode opératoire

The mannitol derivative of Example 7(a) (81 g, 0.311 mol) was suspended in CH2Cl2 (1.1 L) and saturated NaHCO3 (40 mL) and stirred at ambient temperature. Sodium periodate (100 g, 0.47 mol) was added in four portions over 20 minutes and the solution was stirred vigorously at 0° C. for 3 hours. The solvent was decanted off and the remaining solid was stirred in CH2Cl2 and then filtered to remove the excess solid. The two organic portions were combined and concentrated in vacuo. The resulting oil was distilled at reduced pressure to give the title product as a clear, viscous oil. Yield (59 g, 75%). 1H NMR (CDCl3) δ 4.3 (t, 1 H), 3.9 (m, 2 H), 1.4 (d, 6 H).

Source