tert-Butanol → HCID 15674615, compound

Participants

Reaction Steps

Potassium tert-butoxide (0.543 g, 4.83 mM) and t-butyl alcohol (0.525 g, 7.08 mM) were stirred in 15 mL dry THF. The mixture was added to a suspension of carbonyldiimidazole (1.5 g, 9.26 mM) in 15 mL dry THF. The mixture was stirred at room temperature for about 14 h. Phenacyl alcohol (0.643 g, 4.73 mM) was added to the reaction mixture and stirred at 0° C. for 2 h. About 30 mL water was added to the mixture and the carbonate was extracted with (3×50 mL) dichloromethane. The carbonate was purified using 4:1 hexane ethyl acetate. Yield 0.429 g (38%) from 0.643 g phenacyl alcohol, yellow oil; 1H NMR (CDCl3, 400 MHz) δ1.50 (s, 9H), 5.23 (s, 2H), 7.43-7.59 (m, 3H), 7.88 (d, J=7 Hz, 2); 13C NMR (CDCl3, 400 MHz) δ192.3, 153.1, 134.1, 133.9, 128.8, 127.7, 83.0, 67.9, 27.7; FAB-MS, m/z (rel. intensity) 237 (M+1, 13),181 (100), 163 (14), 119 (21), 105 (49), 91 (21), 77 (9), 57 (73); HRMS calcd for (M+1) C13H17O4; 237.1127, found: 237.1135.

Provenance & Evidence