HCID 178488804, compound → HCID 178488805, compound

Participants

Reaction Steps

To a flame-dried round-bottomed flask containing 6-[2'-(tert-butyl)dimethylsilyloxy-4'-bromo-5'-methoxyphenyl]methyl-5,5-dimethylcyclohex-2-en-1-one (13) (0.154 g, 0.454 mmol) in 22 mL ethyl acetate (which had been pre-dried over K2CO3) at room temperature was added 20 mg 5% palladium on carbon, and after flushing / evacuating the vessel 3 times with nitrogen, a hydrogen atmosphere was introduced and maintained by use of a balloon. After 24 h, the flask was again flushed several times with nitrogen, and the contents of the flask were filtered, rinsing with an additional 100 mL ethyl acetate. Rotary evaporation of the solvent afforded 0.156 g (quantitative) of the saturated benzylic ketone as a colorless, viscous oil (Rf 0.67, 2:1 hexanes/ethyl acetate). 1H NMR (400 MHz, CDCl3) δ0.22 and 0.25 [2s, 2×3H, Si(CH3)2 ], 0.87 and 1.12 (2s, 2×3H, geminal-CH3 's), 1.01 [s, 9H, SiC(CH3)3 ], 3.71 (s, 3H, OCH3), 6.79 (s, 1H, 6'-H), 6.91 ppm (s, 1H, 3'-H).

Provenance & Evidence