Ammonium Chloride → (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol

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Reaction Steps

5.8 mmol of (3R,7R)-3,7,11-trimethyl-dodecyl bromide are heated at reflux for 1/4 hour in 20 ml of diethyl ether with etched magnesium. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane and 0.9 g of copper(I) 2-propylacetylide (or 1.2 g of copper(I) bromide-dimethyl sulphide complex) are then added at 0° C. The temperature of the reaction mixture is subsequently left to rise to room temperature and the mixture is stirred for about 16 hours. 10 ml of ammonium chloride are then added and the mixture is extracted with diethyl ether. The extract is dried, concentrated and distilled in a bulb-tube (b.p.0.01 =140° C.). There are obtained 1.28 g (72%) [or 1.41 g (79%)] of (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol as a colourless oil, [α]D20 -0.67° (c=0.9% in CHCl3).

Provenance & Evidence