HCID 16107468, compound → HCID 16107461, compound

Participants

Reaction Steps

To a stirred solution of alcohol 11 (19.0 g, 31.8 mmol) at 0° C. was added dropwise a solution of Jones reagent (2.7 N, 31 mL). After addition, the reaction mixture was stirred at room temperature for 1 hour and 2-propanol (10 mL) was slowly added. The solvent was removed under vacuo and the residue was dissolved in ether. Washing the ether solution with water, separation the layers and the aqueous lay was extracted with ether. The combined organic lay was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give the acid 12 as a solid (18.5 g, 95%). mp. 97-98° C.; 1H NMR (400 MHz, CD3OD) δ 3.62 (s, 2H), 4.25 (d, J=8.8 Hz, 2H), 4.33 (d, J=8.4 Hz, 2H); 19F NMR (376 MHz, CD3OD) δ −71.16 (s); 13C NMR (100.7 MHz, CD3OD) δ 50.9, 53.6, 67.5, 81.2 (m), 121.6 (q, J=292.6 Hz), 171.9; MS (CI) m/z 612 (M++1, 100), 584 (80); HRMS (CI) Calcd for C13H8F18N3O4: 612.0227, Found: 612.0204.

Provenance & Evidence