반응 #2146747

반응 방정식

(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

용매

CH2Cl2

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타The solvent is evaporated
3. 3
   workup.ADDITIONtoluene (100 mL) is added
4. 4
   세척The organic phase is washed with sat. NaHCO3 solution (50 mL) and HCl aq. solution (1N, 50 mL)
5. 5
   건조The organic layers are dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

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.

출처