Methyl acetoacetate → Methyl 3-oxovalerate

Participants

Reaction Steps

According to the method described in Jikken Kagaku Koza, Vol. 19, p. 441, 121 g of methyl 3-ketopentanoate was synthesized from 326 g of methyl acetoacetate and 189 g of propionyl chloride and then subjected to enantioselective hydrogenation using (+)-2,2'-bis[di(p-tolylphosphino)-1,1'-binaphthyl]tetrachlorodiruthenium-triethylamine [Ru2Cl4 (T-BINAP)2Et3N] according to the method disclosed in JP-A-63-310847, to obtain 110 g of methyl R-(-)-3-hydroxypentanoate. 100 g of this compound was treated in the same manner as in Step 1 of Example 1, to obtain 19 g of the desired compound having a boiling point of 60° to 65° C./1 mmHg and a chemical purity, as measured by GC, of 88.2%. The percent yield was 36.3%.

Provenance & Evidence