Acetonitrile → 4,4,5,5,5-Pentafluoro-3-oxopentanenitrile

HRID 1165592Notes

Reaction equation

[C:1](#[N:3])[CH3:2].[F:4][C:5]([F:15])([F:14])[C:6]([F:13])([F:12])[C:7](OCC)=[O:8].C([Li])CCC.CCCCCC>>[F:12][C:6]([F:13])([C:5]([F:15])([F:14])[F:4])[C:7]([CH2:2][C:1]#[N:3])=[O:8]

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 8058Hexane

HCID 67928Propanoic acid, 2,2,3,3,3-pentafluoro-, ethyl ester

HCID 178418339Butyllithium

Product 1

HCID 156138214,4,5,5,5-Pentafluoro-3-oxopentanenitrileYield 77.8%

Procedure

Acetonitrile (4.1 g, 0.10 mole), ethyl pentafluoropropionate (9.61 g, 0.05 mole) and a solution of n-butyllithium in n-hexane (70 ml, 0.11 mole) were reacted according to the same procedure as described in Example 1 to give 7.28 g (77.8%) of the title compound. When the resulting compound was dissolved in CDCl3 and its NMR was measured, the ratio of the keto form/the enol form was found to be 26/74, m.p. 47°-54° C. (deliquescence), b.p. 69°-71° C./18 mmHg.

Sources & evidence

ORD record: ord-756098f85e8e4bd989cd57060ef99d2b
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04910326

Reaction notes

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