Water → HCID 14971843, compound

Participants

Reaction Steps

N-Methyl hydrazine (2.5 mL, 46.6 mmol) was added dropwise to 1-[3-[(1,1-dimethylethyl)dimethylsiloxy]phenyl]-2-[(dimethylamino) methylene]-2-(4,5-diphenyl-2-oxazolyl)ethanone (20) (12 g, 22.8 mmol) and the mixture stirred for about 1 hour, diluted with water, and extracted with dichloromethane. The organic phase was concentrated, and the residue was taken up in THF (150 mL), and tetra-n-butylammonium fluoride (27.84 mL of 1M solution) added. The reaction mixture was stirred about 5 minutes, concentrated, diluted with 1N HCl, and extracted with dichloromethane. Separation by SiO2 chromatography, (elution with 75% ether/hexanes) and recyrstallization from dichloromethane/ether/hexanes gave 3-methyl 2.3 g, (25%), mp 186°-188° C. and 5-methyl 2.85 g (50%), mp 213°-215° C. both as white solids.

Provenance & Evidence