Methyl acetoacetate → Methyl 3-oxo-6-octenoate

HRID 616287Notes

Reaction equation

[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].C(Cl)/C=C/C>>[CH3:10][O:9][C:3](=[O:8])[CH2:4][C:5](=[O:6])[CH2:7][CH2:11]/[CH:12]=[CH:13]/[CH3:14]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 24758Sodium hydride

HCID 637923(2E)-1-Chloro-2-butene

HCID 178418339Butyllithium

Product 1

HCID 6278738Methyl 3-oxo-6-octenoate

Procedure

In accordance with the process of Reference 1, sodium hydride (1.20 g; 50 m mol), methyl acetoacetate (5.70 g; 50 m mol), n-butyl lithium (50 m mol) and trans-crotyl chloride (4.43 g; 50 m mol) were used to obtain 3.60 g of (E)-3-oxo-6-octenoic acid methyl ester.

Sources & evidence

ORD record: ord-28b444a48c3544e0a82859575db53c62
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04073799

Reaction notes

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