2-Methyl-2-butene → HCID 69813108, compound

Participants

Reaction Steps

To a solution of (C5) in dry DCM (0.07 M) was added manganese (IV) oxide. The reaction mixture was stirred at RT for 2 h. Then, the suspension was filtered and the precipitated washed several times with DCM. The combined organic extracts were concentrated to dryness. The resulting crude was dissolved in a mixture of water/tert-butanol (1:1, 0.04 M). Afterwards, 2-methyl-2-butene (20 eq., 2 M in THF), NaH2PO4 (8 eq.) and NaClO2 (8 eq.) were added. The reaction mixture was stirred at RT for 30 min. Then, the mixture was extracted with DCM (3×) and the organic extracts washed with brine (2×) and dried (Na2SO4). Evaporation of the solvent gave the title compound as a yellow powder that was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6, 300K) δ 13.23 (1H, bs), 9.38 (1H, s), 8.45 (2H, d, J=7.3 Hz), 8.12-8.09 (3H, m), 7.91 (1H, d, J=6.8 Hz), 7.52 (1H, t, J=7.0 Hz). MS (ES+) C15H9N3O2 required: 263, found: 264 (M+H)+.

Provenance & Evidence