Isopropanol → HCID 54083316, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the alcohol prepared in 2K (21 mg, 0.067 mmoles) in acetone (2 ml) cooled to 0° C. was added dropwise 2.67M Jones reagent until the organe color was stable. The mixture was stirred 15 min at 0° C. The excess of Jones reagent was reacted with isopropanol. The acetone was evaporated under reduced pressure without heating. The residue was taken with water and extracted three times with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to leave an oil (20 mg). Flash chromatography on silicagel and elution with a 25:75 mixture of ethyl acetate and hexane gave pure title acid (14 mg, 64%). NMR (H1, CDCl3, 360 MHz): 0.89 (t, JHH ~7 Hz, 3), 1.21 to 1.45 (m, 10), 1.51 (quint, JHH ~7 Hz, 2), 1.98 to 2.12 (m, 8), 2.37 (t, JHH ~7 Hz, 2), 2.96 (dd, JHF =23 Hz, JHH =6.8 Hz, 2), 4.98 (dt, JHH =21.2Hz, JHH =7.9 Hz, ]), 5.3 to 5.5 (m, 4).

Provenance & Evidence