A Useful Synthesis of Chiral Glyoxylates

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• Alternatively, crude fumaroyl chloride may be obtained by distilling off the excess SOCl2 (until the boiling temp, reaches 157°C). The undistilled oily residue is used at once or kept under Ar in a well-stoppered flask. Final yields of the purified fumarates are about the same using either the crude or the distilled chloride
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• Lewatit S-100 (from Bayer Hispania CSA) was previously activated by shaking with 1M HCl, and dried on filter paper
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• A. water separator for organic solvents heavier than water is placed between the flask and the condenser
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• The H NMR spectrum of this material was almost identical to that of the product of method A. except for a new singlet at δ4.62 ppm, that was assigned to-(CHOH)2-in the meso form. Signals at δ 4.50 ppm and δ 4.62 ppm were respectively in the ratio 80:20, and together integrated for 1H
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• Samples obtained by methods A and B give similar results
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