Methyl acetoacetate → 6-Octynoic acid, 3-oxo-, methyl ester

HRID 616288Notes

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].BrCC#CC>>[CH3:10][O:9][C:3](=[O:8])[CH2:4][C:5](=[O:6])[CH2:7][CH2:11][C:12]#[C:13][CH3:14]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 24758Sodium hydride

HCID 27568621-Bromo-2-butyne

HCID 178418339Butyllithium

Product 1

HCID 114692956-Octynoic acid, 3-oxo-, methyl ester

Procedure

In accordance with the process of Reference 1, sodium hydride (550 mg; 23 m mol), methyl acetoacetate; (2.56 g; 22 m mol), n-butyl lithium (23 m mol) and 4-bromo-2-butyne were used to obtain 2.53 g of 3-oxo-6-octynoic acid methyl ester.

Sources & evidence

ORD record: ord-ca0c92fc0af64ec7b210e2e8c8eab5f8
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04073799

Reaction notes

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