Hydrochloric Acid → HCID 21469712, compound

Participants

Reaction Steps

A solution of 3-trimethylsilylbenzoic acid in methylene chloride (12 ml) was cooled to -22° C. and N-methylmorpholine (2.0 ml) was added. To the mixture isobutylchloroformate (0.88 ml) was added. The mixture was stirred for 25 min. followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.9 g). The mixture was stirred at -22° C. for 1 hr., allowed to warm to room temperature and stirred for 1.5 hr. The reaction mixture was poured into dil HCl and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic extracts were washed with dil NaHCO3 and dried over Na2 SO4. The solvent was removed in vacuo and the crude product purified by flash chromatography (10% EtOAc in hexane) to yield 600 mg of the desired product. HRMS calc. 238.1263. Found: 238.1268.

Provenance & Evidence