Sulfuric Acid → HCID 19025070, compound

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).

1. temperaturethe reaction mixture was heated
2. concentrationThe reaction mixture was concentrated at reduced pressure
3. dissolutionthe residue was dissolved in ether (40 mL)
4. washwashed with saturated aqueous NaHCO3 (2×10 mL)
5. dry with materialThe organic solution was dried (MgSO4)
6. concentrationconcentrated

ORD record

ord-64fa4781d54f429290cbb53e312e0d54

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05312950