Réaction #2146747

Équation de réaction

(3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol

trichloroisocyanuric acid

TEMPO

→

(4R,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-dihydrofuran-3-one

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   AutreThe solvent is evaporated
3. 3
   workup.ADDITIONtoluene (100 mL) is added
4. 4
   LavageThe organic phase is washed with sat. NaHCO3 solution (50 mL) and HCl aq. solution (1N, 50 mL)
5. 5
   SéchageThe organic layers are dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Mode opératoire

To a solution of (3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol (9.20 g, 19.08 mmol) in anhydrous CH2Cl2 (70 mL) and trichloroisocyanuric acid (4.88 g, 21 mmol) in an ice bath is added TEMPO (160 mg, 0.95 mmol). The reaction mixture changes to a yellow suspension and is stirred at 20° C. for 1 h. The reaction is determined to be complete by HPLC and filtered. The solvent is evaporated and toluene (100 mL) is added. The organic phase is washed with sat. NaHCO3 solution (50 mL) and HCl aq. solution (1N, 50 mL). The organic layers are dried (MgSO4), filtered and concentrated to give (4R,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-dihydrofuran-3-one as light green oil which is directly used for the next step.

Source