反应详情

温度

-78 °C

A solution of 2-dodecyl-α-hydroxy-α-phenyl-2H-tetrazole-5-acetic acid, ethyl ester (0.45 g, 1.08 mole) in CH2Cl2 (2 mL) was added dropwise to a -78° C. solution of diethyl amino sulfur trifluoride (DAST, J. Org. Chem. 1975;(40):574:578, 0.15 mL, 1.1 mole) in CH2Cl2 (1 mL) under dry nitrogen. The mixture was stirred for 60 minutes at -78° C. before the cooling bath was removed and the solution allowed to warm to room temperature, where it was stirred an additional 3 hours. The mixture was poured into ice water and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with brine (50 mL) and dried. Filtration and concentration produced an oil which was flash chromatographed (silica gel, 7:1 hexane-ethyl acetate) to afford 0.3 g (66%) of the title compound as an oil.

1. customwas removed
2. temperatureto warm to room temperature
3. stirringwhere it was stirred an additional 3 hours
4. additionThe mixture was poured into ice water
5. extractionextracted with ethyl acetate (2×100 mL)
6. washThe combined ethyl acetate extracts were washed with brine (50 mL)
7. customdried
8. filtrationFiltration and concentration
9. customproduced an oil which
10. customchromatographed (silica gel, 7:1 hexane-ethyl acetate)