Methyl acetoacetate → Methyl 3-oxovalerate
Reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:9](Cl)(=O)CC>>[O:4]=[C:3]([CH2:5][CH3:9])[CH2:2][C:1]([O:7][CH3:8])=[O:6]Participants
3
Procedure
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%.
Sources & evidence
- ORD record
- ord-54719abd20fc49a99238e9b5d8a8e1e6
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05221755
Reaction notes
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