3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

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Reaction Steps

3-Hydroxybenzaldehyde (70 g, 0.57 mol), tert-butyldimethylsilyl chloride (92 g, 0.61 mol), and imidazole (92 g, 1.35 mol) were combined in dimethylformamide (250 mL). The mixture was stirred at room temperature, under nitrogen, for 1 hour. The solution was poured into water (1.5 L) and extracted with 2×500 mL petroleum ether (35°-60° C. boiling range). The organic solution was washed with saturated sodium chloride solution (100 mL), dried over magnesium sulfate, treated with silica gel (20 g), filtered, and concentrated in vacuo. The residue was dried further under high vacuum to yield 126.6 g (94%) of the air and light-sensitive 3-((tert-butyldimethylsilyl)oxy)benzaldehyde as an amber oil. NMR (300 MHz, CDCl3): δ 0.22 (s, 6H); 0.99 (s, 9H); 7.10 (ddd, J1 =1.2 Hz, J2 =2.5 Hz, J3 =7.9 Hz, 1H); 7.32 (dd, J1 =1.5 Hz, J2 =2.4 Hz, 1H); 7.39 (t, J=7.8 Hz, 1H); 7.47 (ddd, J1 =1.3 Hz, J2 1.3 Hz, J3 =7.6 Hz, 1H); 9.95 (s, 1H). Mass spectrum (CI--CH4) m/e: 237 (M+1, 100%). Calculated for C13 H20O2Si: C, 66.05; H, 8.53. Found: C, 65.95; H, 8.56.

Provenance & Evidence