Propionitrile → 2-(Pentafluoropropionyl)propionitrile

HRID 2291693Notes

Reaction equation

HRID 2291693 reaction equation
[C:1](#[N:4])[CH2:2][CH3:3].[F:5][C:6]([F:16])([F:15])[C:7]([F:14])([F:13])[C:8]([O:10]CC)=O.C([Li])CCC.CCCCCC>>[F:14][C:7]([F:13])([C:6]([F:5])([F:15])[F:16])[C:8]([CH:2]([CH3:3])[C:1]#[N:4])=[O:10]

Participants

5

Reactant 4

HCID 7854PropionitrileHCID 8058HexaneHCID 67928Propanoic acid, 2,2,3,3,3-pentafluoro-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 156138222-(Pentafluoropropionyl)propionitrile

Procedure

Propionitrile (13.2 g, 0.24 mole), ethyl pentafluoropropionate (23.05 g, 0.12 mole) and a solution of n-butyllithium in n-hexane (168 ml, 0.264 mole) were reacted as the procedure illustrated in the preceding Preparation 1 to give 22.72 g (crude yield 94.1%) of the crude title compound. The yield calculated as the pure product was 84.1%. The resulting compound was dissolved in CDCl3 to measure NMR, the ratio of the keto form/the enol form was found to be 71/29, b.p. 63°-65° C./28 mmHg.

Workup

  1. customillustrated in the preceding Preparation 1

Sources & evidence

ORD record
ord-a832b1eeb63e41b08b26873ac0d9f6d0
Source dataset
uspto-grants-1989_01
Patent number
US04797492

Reaction notes

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