Tetrahydrofuran → 1-(1-Benzyloxymethylimidazol-2-yl)-2-methyl-1-propanol

Participants

Reaction Conditions

Reaction Steps

1-benzyloxymethylimidazole prepared according to the procedure of Ngochindo, R., J. Chem. Res. (S), 58 (1990)) (3.76 g, 20 mmol), and THF (40 mL) at -40° C., was treated dropwise with n-BuLi (8.4 mL, 21 mmol, 2.5M in hexane). The resulting solution was stirred at -40° C. for 15 min, and i-butyraldehyde (2.0 mL, 22 mmol) was added dropwise. The reaction was stirred at -40° C. for 1.5 h, 0° C. for 1 h, warmed to 23° C., poured into H2O, and extracted with EtOAc. The combined ekhracts were washed with brine, dried (Na2 SO4) and concentrated in vacuo. Trituration of the residue with Et2O/hexane gave a white solid which was dried in vacuo overnight to afford of the title compound (3.57 g, 69%). 1H NMR(CDCl3, 400 MHz) δ 7.28 (m, 5H), 6.97 (s, 1H), 6.92 (s, 1H), 5.23 (d, 1H, J=12 Hz), 5.42 (d, 1H, J=12 Hz), 4.48 (s, 2H), 4.44 (d, 1H, J=9 Hz), 2.21 (m, 1H), 1.02 (d, 3H, J=7 Hz), 0.83 (d, 3H, J=7 Hz).

Provenance & Evidence