Compound 7

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InChIKey XSSMPLRGNJEXLF-FAEUDGQSSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

6 (50 mg, 0.16 mmol) was suspended in triethylaminetrihydrofluoride (1 mL) and heated by microwave irradiation (50 W, 120 ˚C) in a Teflon flask for 2 h. The reaction mixture was cooled to RT, and the resulting pale yellow residue was reconstituted with ethyl acetate (10 mL) and poured into saturated aqueous sodium hydrogen carbonate solution (10 mL). The layers were separated, and the aqueous phase was re-extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine (10 mL), dried over MgSO₄, filtered and concentrated in vacuo, affording a colourless residue. Purification of the residue by silica gel chromatography, eluting with dichloromethane and methanol (97:3 to 95:5), furnished (1s,2R,3R,4s,5S,6S)-2,3,4,5,6-pentafluorocyclohexan-1-ol 7 (12 mg, 40%) as a colourless solid; ¹H NMR (500 MHz, CDCl₃+MeOD): δ 5.23–5.02 (m, 2H, H-3 and H-5), 4.76–4.54 (m, 1H, H-4), 4.48–4.29 (m, 3H, H-2, H-6 and CHOH H-1); ¹⁹F{¹H} NMR (470 MHz, CDCl₃+MeOD): δ -210.1 (br s, 2F, F-2 and F-6), -212.9 (br s, 1F, F-4), -214.4 (br s, 2F, F-3 and F-4); HRMS-ESI⁺ (m/z): [M+Na]⁺ calcd. for C₆H₇OF₅Na, 213.0309; found, 213.0307.