3219-63-4

1-Trimethylsilylmethanol is used as nucleophile to resolve the racemate obtained from enantioselective esterification of naproxen (2-(6-methoxy-2-naphthyl) propionic acid) by lipases. It was also used as a nucleophilic hydroxymethylation agent.

If the NMR indicates impurities (should have only two signals), then dissolve it in Et2O, shake this with aqueous 5N NaOH, M H2SO4, saturated aqueous NaCl, dry (MgSO4) and distil it using an efficient column at atmospheric pressure. The 3,5-dinitrobenzoate has m 70-70.5o (from 95% EtOH). [Huang & Wang Acta Chem Sin 23 291 1957, cf. Chem Abstr 52 19911 1958, Speier et al. J Am Chem Soc 81 1844 1959 and Speier et al. J Am Chem Soc 70 1117 1948, Beilstein 4 III 1844, 4 IV 2876.]