Реакция #2146747

Уравнение реакции

(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

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered
2. 2
   ДругоеThe solvent is evaporated
3. 3
   workup.ADDITIONtoluene (100 mL) is added
4. 4
   ПромывкаThe organic phase is washed with sat. NaHCO3 solution (50 mL) and HCl aq. solution (1N, 50 mL)
5. 5
   СушкаThe organic layers are dried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

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.

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