Ethyl Acetoacetate → Ethyl 3-Hydroxybutyrate

HRID 1075704Notes

Reaction equation

HRID 1075704 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]>CO.O>[OH:1][CH:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 1

HCID 8868Ethyl Acetoacetate

Product 1

HCID 62572Ethyl 3-Hydroxybutyrate

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The same procedure of Example 5 is repeated with the only differences that 1.95 g of ethyl 3-oxo-butyrate were weighed and dissolved in MeOH/H2O 19/1 (v/v) and the catalyst of Example 15 was utilized. At the end of the reaction, the ethyl 3-hydroxybutyrate resulted to be equal to 91%, while the ethyl 3-dimetoxybutyrate resulted equal to 9%. The stereoinduction was <99% in favour of the antipode (S).

Workup

  1. customAt the end of the reaction

Sources & evidence

ORD record
ord-02a2956a34bd4a4082e0e1b1ad37d53d
Source dataset
uspto-grants-1999_05
Patent number
US05907045

Reaction notes

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