Diethyl Ether → HCID 19780704, compound

Participants

Reaction Conditions

Reaction Steps

A 3M ethereal solution of methylmagnesium iodide (8 ml, 24 mM) was added dropwise to a stirred solution of the lactone (C) (1.8 g, 9.5 mM) in ether (42 ml) at 5° C. Stirring was continued at ambient temperature for 12 hours. The mixture was then cooled to 5° C., treated with excess saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and the solvent removed by evaporation. The residual oil was purified by flash chromatography, eluting with dichloromethane/ethyl acetate (9:1 v/v increasing in polarity to 8:2 v/v) to give 5-(2-hydroxy-4,6-dimethylphenyl)-2-methylpentan-2-ol (D) (1 g, 48% yield), m.p. 128° C. (after recrystallisation from cyclohexane); NMR (d6 -DMSO): 0.95(6H,s), 1.33(4H,m), 1.97(3H,s), 2.01(3H,s), 2.37(2H,s), 6.24(1H,s), 6.28(1H,s); microanalysis, found: C, 75.6; H,10.2%; C14H22O2 requires: C,75.6; H,10.0%.

Provenance & Evidence