Sulfuric Acid → HCID 19025070, compound

Participants

Reaction Steps

Concentrated sulfuric acid (18M; 0.1 mL; 2 mmol; 0.02 equiv.) was added to 80 mL of tert-butanol. Butadiene monoepoxide (8.05 mL; 100 mmol) was added and the reaction mixture was heated to reflux overnight (15 h) to completely consume butadiene monoepoxide by GC analysis. The reaction mixture was concentrated at reduced pressure and the residue was dissolved in ether (40 mL) and washed with saturated aqueous NaHCO3 (2×10 mL). The organic solution was dried (MgSO4) and concentrated, and the crude product was fractionated in vacuo, affording pure 1j (3.12 g; 22%), bp 42°-45°/1 mm Hg along with an impure fraction, 3.83 g, bp 45°-85°/1 mm Hg. 1H nmr (300 MHz, CDCl3): 5.797 (1H, ddd, J=6.29, 10.57, 17.07 Hz); 5.260 (1H, d, J=17.22 Hz); 5.144 (1H, d, J=10.50 Hz); 4.092 (1H, br q, J=5.76 Hz); 3.469 (1H, dd, J=4.45, 11.07 Hz); 3.399 (1H, dd, J=7.63, 11.14 Hz); 2.0 (1H, br s); 1.218 (9H, s).

Provenance & Evidence