tert-Butanol → HCID 66588522, compound

Participants

Reaction Steps

To a solution of tert-butanol (28.2 μL, 296 μMol) in dichloromethane (4 mL) was added Dess-Martin Periodinane [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (116 mg, 274 μMol), and the resulting mixture was stirred under argon at room temperature for 10 minutes. A solution of alcohol 4 (R=Et, mixture of isomers) in dichloromethane (2 mL) was added to the mixture and stirred at room temperature for 3 hours. The mixture was diluted with 4 mL ethyl acetate and stirred vigorously with aqueous 1.5:1:1 saturated sodium sulfite:saturated sodium bicarbonate:brine (3.5 mL) for a period of 1 hour. The phases were separated and the aqueous phase was re-extracted with ethyl acetate (3 mL). The combined organics were washed with brine (2 mL), dried (anhydrous Na2SO4), filtered, and evaporated. Preparative TLC using dichloromethane as the developing solvent afforded 91 mg (52%) of compound 14 as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.35-6.90 (m, 25H), 6.80 (m, 2H), 4.96 (m, 3H), 4.55 (m, 4H), 4.11 (m, 3H), 3.94 (m, 2H), 3.79 (m, 3H), 3.47 (s, 1H), 2.83 (m, 1H), 2.62 (q, J=7.8 Hz, 2H), 1.16 (t, J=7.5 Hz, 3H). LC-ESI-MS m/z 766 (M+H), 788 (M+Na).

Provenance & Evidence