Dimethyl Sulfoxide → Dimethyl 1,1-difluoro-2-oxo-4,8,12-trimethyl-3,7,11-tridecatrienylphosphonate

Combine trifluoroacetic acid anhydride (1.30 mL, 0.0096 mol) with dichloromethane (20 mL) and cool to -60° C. Add dropwise a solution of dimethylsulfoxide (1.30 mL, 0.0183 mol) in dichloromethane (2 mL) while maintaining the temperature below -55° C. After addition is complete, stir for stir for 2 minutes. Add a solution of the dimethyl 1,1-difluoro-2-hydroxy-4,8,12-trimethyl-3,7,11-tridecatrienylphosphonate (1.60 g, 0.0042 mol) prepared in example 1 in dichloromethane (4 mL) and stir for 45 minutes. Cool the reaction to -78° C. and add triethylamine (3.0 mL, 0.021 mol) dropwise. Allow the reaction to warm to ambient temperature and stir for 45 minutes. Pour the reaction into water (100 mL). Extract this mixture with diethyl ether (400 mL). Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (20% ethyl acetate/hexane, Rf =0.18) to provide the title compound (1.1 g, 69%) as an oil.

1. temperaturewhile maintaining the temperature below -55° C
2. additionAfter addition
3. stirringfor stir for 2 minutes
4. stirringstir for 45 minutes
5. temperatureCool
6. customthe reaction to -78° C.
7. customthe reaction
8. stirringstir for 45 minutes
9. additionPour
10. extractionExtract this mixture with diethyl ether (400 mL)
11. dry with materialDry the organic phase over anhydrous magnesium sulfate
12. filtrationfilter
13. concentrationconcentrate under vacuum
14. customPurify the residue by flash chromatography (20% ethyl acetate/hexane, Rf =0.18)

ORD 기록

ord-263c998acccd434e8b020e7b4e2d3d48

출처 데이터셋

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05665715