Toluene → Diethyl thiophosphate

Participants

Reaction Steps

Compound Spinosyn H (261 mg, 0.364 mmol) was dissolved in dry pyridine (3 ml). DMAP (60 mg) was added, followed by diethyl chlorothiophosphate (152 mg, 125 μl, 0.80 mmol). The reaction mixture was stirred at RT under nitrogen. After 12 hrs. toluene (50 ml) and EtOAc (50 ml) were added. The solution was extracted with brine, then with 5% aq. NaHCO3. The organic layer was dried over and Na2SO4 and concentrated in vacuo. The residue was purified over a flash SiO2 column (30 g/EtOAc) to give compound 2'R)-(diethyl)thiophosphate of Spinosyn H; 84 mg, 27%) CI MS m/z 870 (M+1); 1H-NMR (CDCl3) δ 6.74 (1H, bs), 4.80 (1H, m), 4.22 (4H, 2× CH2, m), 1.30 (6H, 2× CH3, m).

Provenance & Evidence