Ethyl bromoacetate → Ethyl 4-oxo-3-propanoylhexanoate

HRID 615018Notes

Reaction equation

[CH3:1][CH2:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Br)[CH3:11]>>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[C:5](=[O:8])[CH2:6][CH3:7])[CH3:11]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 819233,5-Heptanedione

Product 1

HCID 50988004Ethyl 4-oxo-3-propanoylhexanoate

Procedure

By a method analogous to that described in Example 34, 3,5-heptane dione was reacted with bromoacetic acid-ethyl ester to form 3,3-dipropionyl-propionic acid-ethyl ester, which was further reacted with phenylhydrazine to produce 3,5-diethyl-1-phenyl-pyrazol-4-acetic acid-ethyl ester which was saponified to form the free acid. Obtained was 3,5-diethyl-1-phenyl-pyrazol-4-acetic acid having a melting point of 129°-130° C.

Sources & evidence

ORD record: ord-e58c3128a5a94739badde8765e2a7b2d
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146721

Reaction notes

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