Dicyclohexylcarbodiimide → Ethyl 6,6,6-trifluoro-3-oxohexanoate

To a stirred solution of Meldrum's Acid (3.0 g, 20.8 mmol) in 100 mL of CH2Cl2, 4-trifluoromethyl butyric acid (2.96 g, 20.8 mmol) was added followed by DMAP (5.08 g, 41.6 mmol) and finally DCC (4.30 g, 20.8 mmol). The reaction stirred overnight at room temperature. The mixture was then filtered and the filtrate washed with 1M HCl, H2O and Brine. The organics were then dried over sodium sulfate, filtered and concentrated to a yellow oil. The material was then dissolved in 100 mL of EtOH and refluxed overnight. The reaction mixture was concentrated and purified by column chromatography (ethyl acetate/hexanes (1:4)) to yield 1.88 g (43%) of a clear oil.: 1H NMR (CDCl3, 400 MHz) δ 4.24–4.10 (q, 2H, J=7.14), 3.45 (s, 2H), 2.93–2.73 (t, 2H, J=7.88), 2.52–2.28 (m, 2H), 1.31–1.20 (t, 3H, J=7.14)

1. filtrationThe mixture was then filtered
2. washthe filtrate washed with 1M HCl, H2O and Brine
3. dry with materialThe organics were then dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated to a yellow oil
6. dissolutionThe material was then dissolved in 100 mL of EtOH
7. temperaturerefluxed overnight
8. concentrationThe reaction mixture was concentrated
9. custompurified by column chromatography (ethyl acetate/hexanes (1:4))

ORD record

ord-059775a64cb34e02a03a797fd62f7a2d

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189851B2