Ammonium Chloride → HCID 22630149, compound

Participants

Reaction Steps

To a stirred 1 M etheral solution of allylmagnesium bromide (20 ml, 20 mmol) was added dropwise a solution of 3,3-diethyl-5,5-dimethylcyclohexanone (25) (1.47 g, 8.06 mmol) in dry ether (5 ml). The mixture was stirred for 1 h at ambient temperature and boiled at reflux for 10 min. Then it was cooled with ice water and treated with saturated aqueous NH4Cl (40 ml). The organic layer was separated and washed with water and brine. After drying over anhydrous MgSO4, the solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel (light petroleum ether). A fraction with Rf 0.7 (Hexane:EtOAc, 13:2) was collected. Evaporation of the solvent afforded 26 (1.35 g, 74%) as a colorless oil. 1H NMR (CDCl3, TMS): 0.74 (6H, t, 7 Hz, 2CH3 of ethyl); 0.88 (3H, s, 5-CH3eq); 1.19 (3H, s, 5-CH3ax); 0.80-2.05 (10H, m, 2,4,6-CH2 and 2CH2 of ethyl); 2.14 (2H, d, 7 Hz, CH2C═); 4.95-5.30 (2H, m, ═CH2) and 5.65-6.20 ppm (1H, m, ═CH).

Provenance & Evidence