HCID 18977580, compound → HCID 22904118, compound

Participants

Reaction Steps

An atmosphere of hydrogen was introduced to and maintained by a balloon to an evacuated 50 mL round-bottomed flask containing 6-(4'-nitrophenyl)methyl-5,5-dimethylcyclohex-2-en-1-one (39) (14.0 mg, mmol) and tris(triphenylphosphine)rhodium chloride (Wilkinson's catalyst) (8.0 mg) in 6.5 mL anhydrous benzene. The yellow-orange solution was stirred at room temperature for 24 h, and then passed through a short silica gel column (hexanes/ethyl acetate, 3:1) to afford the 6.8 mg (48%) of the desired ketone as a pale yellow oil (Rf0.43, 2:1 hexanes lethyl acetate). 1H NMR (400MHz, CDCl3) δ0.86 and 1.23 (2s, 2×3H, geminal-CH3 's), 2.50 (d, 1H, J=13.0 Hz, 2-H), 2.66 and 3.17 (d of ABq, 2H, JAB =13.0 Hz, JA =1.6 Hz, JB =9.6 Hz, benzylic-CH2), 7.37 (d, 2H, J=9.6 Hz, 2', 6'-H), 8.09 ppm (d, 2H, J=9.6 Hz, 3',5'-H). [Compound 40 is hereinafter also referred to as COMPOUND "V" or 120211]

Provenance & Evidence