Reaction #2200602

Reaction equation

product

1-O-methyl-2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranose

SnCl4

→

1-O-methyl-3,5-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranose

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.WAITthe solution was kept at 3° C. overnight
2. 2
   OtherAfter 43 hours the reaction was quenched
3. 3
   workup.ADDITIONby carefully adding the solution to 1.9 L saturated NaHCO3 solution
4. 4
   OtherTin salts were removed via filtration through celite after which the organic phace
5. 5
   Otherwas isolated
6. 6
   Dryingdried with MgSO4
7. 7
   Otherevaporated in vacuo
8. 8
   OtherThe crude oil was used directly in the next step without further purification

Procedure

To a solution of the product of Step 1 (171.60 g, 0.2676 mol) in 1.8 L CH2Cl2 that was cooled to 0° C., was added dropwise a solution of stannous chloride (31.522 mL, 0.2676 mol) in 134 mL CH2Cl2 while stirring. After the solution was kept at 3° C. for 27 hours, another 5.031 ml of SnCl4 (0.04282 mol) was added and the solution was kept at 3° C. overnight. After 43 hours the reaction was quenched by carefully adding the solution to 1.9 L saturated NaHCO3 solution. Tin salts were removed via filtration through celite after which the organic phace was isolated, dried with MgSO4 and evaporated in vacuo. The yield of raw, dark yellow oil was 173.6 g, which contains 2,4-dibenzoyl chloride. The crude oil was used directly in the next step without further purification.

Source