Imidazole → HCID 58025809, compound

Participants

Reaction Conditions

Reaction Steps

O-vanillin (26.3 mmol) is mixed with TIPSCl (39.6 mmol) and imidazole (78.7 mmol) in a microwave vessel. The mixture is heated in the microwave at 100° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying with MgSO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as an oil: 1H NMR (400 MHz, CDCl3) δ 10.6 (s, 1H), 7.38 (dd, J1=1.6 Hz, J2=8 Hz, 1H), 7.04 (dd, J1=1.6 Hz, J2=8 Hz, 1H), 6.93 (td, J1=8 Hz, J2=0.8 Hz, 1H), 3.82 (s, 3H), 1.34-1.25 (m, 3H), 1.1 (s, 18H); LC/MS (ES+): 309 (M+1)+.

Provenance & Evidence