Réaction #487536

Équation de réaction

TsCl

triethylamine

TsCl

Diethyl 3-hydroxy-1,1-difluoro-propylphosphonate

→

Diethyl 3-tosyloxy-1,1-difluoro-propylphosphonate

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreAfter 30 m, the reaction mixture was partitioned between water and CH2Cl2
2. 2
   FiltrationThe organic layer was filtered
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 1:1 hexanes
5. 5
   LavageThe column was eluted with hexanes-ethyl acetate

Mode opératoire

Diethyl 3-hydroxy-1,1-difluoro-propylphosphonate [1225194-19-3](4.4 g, 0.019 mol) was dissolved in CH2Cl2 (20 mL) and triethylamine (7.7 g) and treated with TsCl (5.4 g, 0.029 mol) followed by DMAP (0.23 g, 0.0019 mol) at rt for 2 h. After 2 h, an additional portion of TsCl (0.6 g) was added. After 30 m, the reaction mixture was partitioned between water and CH2Cl2. The organic layer was filtered and concentrated in vacuo. The residue was dissolved in 1:1 hexanes:CH2Cl2 (100 mL) and applied to 85 g flash silica gel (topped with Na2SO4 and equilibrated with hexanes). The column was eluted with hexanes-ethyl acetate. Intermediate 23 weighed 6.3 g (94%). 1H NMR (CDCl3) 7.2-7.8 (AB, 4H); 3.9-4.4 (m, 6H); 2.0-3.0 (m, 5H), 1.4 (t, 6H).

Source