Hydrochloric Acid → HCID 19979830, compound

Participants

Reaction Steps

155 mg (1 mM) of (-)-2-cyano-2-methylhexanoic acid ([α]D -6.15 degrees (c1, methanol)) and 2 ml of thionyl chloride were placed in a dried flask and heat-refluxed in a nitrogen atmosphere, followed by distilling-off of excessive thionyl chloride under reduced pressure. To the resultant acid chloride was added a solution of 312 ml (1 mM) of 4-(5-n-decyl-2-pyrimidyl)phenol and 240 mg (2 mM) of triethylenediamine in 2.5 ml of dry benzene, followed by 2 hours of reaction at 50° C. Further, a solution of 80 mg (2 mM) of sodium hydride in dry benzene was added thereto, followed by 2 hours of reactions. After the reaction, the mixture was cooled to room temperature, followed by addition of 1N-hydrochloric acid and distilled water and extraction with ether. The resultant ether layer was dried on sodium sulfate, followed by distilling-off of the solvent and purification by thin layer chromatography (developer solvent: methylene chloride) to obtain 59 mg of p-(5-n-decyl-2-pyrimidyl)phenyl 2-cyano-2-methylbexanoate. Yield: 11.3% [α]D -3.5 degrees (c1, methylene chloride) m.p.=38°-43° C.

Provenance & Evidence