[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[O:3].Br[CH:8]([CH2:13][OH:14])[C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].C(=O)=O>CCCCCC>[O:14]1[CH2:13][CH:8]([C:9]([O:11][CH3:12])=[O:10])[O:3][CH:2]1[C:1]([O:5][CH3:6])=[O:4]
Methyl glyoxylate 11.3 g (0.128 mol) and methyl 2-bromo-3-hydroxypropionate 31 g (0.129 mol) were mixed and the mildly exothermic reaction allowed to cool. The mixture was then treated with hexane (50 ml) and 17.8 g (0.129 mol) potassium carbonate. Evolution of CO2 was sluggish; the mixture was warmed to 45° and allowed to stir overnight. The work-up as described in Example 1 yielded after ether removal, 13.0 g of a light yellow liquid. Distillation in vacuo gave 5.2 g (21%) of the title compound bp 84°-86° at 0.3 mm Hg as a clear colorless liquid. Analysis by GlPC indicated >96% purity, and the pmr spectrum indicated a mixture of trans & cis isomers approximately 70-80% trans.
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