Реакция #487536

Уравнение реакции

TsCl

triethylamine

TsCl

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

→

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

Растворители

CH2Cl2

Условия реакции

Обработка

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

Методика

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).

Источник