반응 #487536

반응 방정식

TsCl

triethylamine

TsCl

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

→

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

용매

CH2Cl2

반응 조건

후처리

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

실험 절차

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).

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