Nitrogen → 1-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol

참여 물질

반응 조건

반응 단계

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde (3.79 g, 17.14 mmol) in THF (173.0 mL) was treated at −78° C. with methylmagnesium bromide (17.1 mL of a 1M solution in THF, 17.14 mmol). The reaction mixture was stirred at −78° C. for 4 h then poured on sat. aq. NH4Cl (150 mL) and extracted with EA (2×300 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil. TLC: rf (50:50 hept-EA)=0.24. LC-MS-conditions 02: tR=0.79 min. 1H NMR (400 MHz, CDCl3) δ 1.55 (d, J=6.5 Hz, 3H), 2.09 (d, J=5.0 Hz, 1H), 4.83-4.95 (m, 1H), 5.31 (s, 2H), 6.28 (d, J=3.0 Hz, 1H), 6.46 (d, J=3.0 Hz, 1H), 8.09 (s, 1H), 8.13 (s, 1H).

출처 및 근거