Tetrahydrofuran → Methyl 6,6-dichloro-3,3-dimethyl-5-hydroxy-7,7,7-trifluoroheptanoate

温度

-78 °C

To an agitated mixture of methyl 3,3-dimethyl-5-oxopentanoate (1.0 g), 1,1-dichloro-2,2,2-trifluoroethane (1.06 g) and dry tetrahydrofuran (10 cm3), maintained at -78° C., was added, over a period of 5 minutes, sodium t-butoxide (1.66 cm3 of a 42% w/w solution in dimethylformamide) after which the mixture continued to be agitated at -78° C. for a further 60 minutes. The reaction was quenched with saturated ammonium chloride at low temperature and the mixture allowed to warm to the ambient temperature. After addition of water (20 cm3) and separation of the organic phase, the aqueous phase was extracted with di-isopropyl ether (3×30 cm3) and the extracts combined with the organic phase, which was washed with brine (2×10 cm3) and dried over anhydrous magnesium sulphate. After removal of the volatile components by evaporation under reduced pressure the residual oil was purified by column chromatography (silica gel column eluted with a 9:1 mixture (by volume) of hexane and ethyl acetate) to give methyl 6,6-dichloro-3,3-dimethyl-5-hydroxy-7,7,7-trifluoroheptanoate as a colourless oil (yield 56%).

1. additionwas added, over a period of 5 minutes
2. customThe reaction was quenched with saturated ammonium chloride at low temperature
3. temperatureto warm to the ambient temperature
4. additionAfter addition of water (20 cm3) and separation of the organic phase
5. extractionthe aqueous phase was extracted with di-isopropyl ether (3×30 cm3)
6. washwas washed with brine (2×10 cm3)
7. dry with materialdried over anhydrous magnesium sulphate
8. customAfter removal of the volatile components
9. customby evaporation under reduced pressure the residual oil
10. customwas purified by column chromatography (silica gel column
11. washeluted with a 9:1 mixture (by volume) of hexane and ethyl acetate)

ORDレコード

ord-fec4156088a747fbb75f270d898a77ee

出典データセット

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05756835