HCID 69205118, compound → HCID 69205163, compound

Participants

Reaction Steps

To a solution of [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3-ethoxy-4-methoxy-phenyl)-methanol (6.5 g, 15.6 mmol) in CH2Cl2 (200 mL) was added manganese dioxide (2.65 g, 26.1 mmol), and the mixture was stirred at ambient temperature for 16 h. Manganese dioxide (2.65 g, 26.1 mmol) was again added, and stirring proceeded for an additional 7 h. The mixture was filtered through Celite, and the sicciate was washed with CH2Cl2 (50 mL). The filtrate was evaporated, providing [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3-ethoxy-4-methoxy-phenyl)-methanone as an oil (6.2 g, 96% yield): 1H NMR (CDCl3) δ 0.17 (s, 6H, 2SiCH3), 1.00 (s, 9H, SiC(CH3)3), 1.49 (t, J=7.0 Hz, 3H, OCH2CH3), 3.89 (s, 3H, OCH3), 3.95 (s, 3H, OCH3), 4.16 (q, J=7.0 Hz, 2H, OCH2CH3), 6.87-6.92 (m, 2H, Ar), 7.33-7.43 (m, 4H, Ar).

Provenance & Evidence