Acetonitrile → Hexanenitrile, 4-ethyl-4-methyl-3-oxo-

HRID 2166188Notes

Reaction equation

HRID 2166188 reaction equation
[CH2:1]([C:3]([CH3:10])([CH2:8][CH3:9])[C:4]([O:6]C)=O)[CH3:2].[C:11](#[N:13])[CH3:12].[H-].[Na+]>O1CCCC1>[C:11]([CH2:12][C:4]([C:3]([CH2:1][CH3:2])([CH3:10])[CH2:8][CH3:9])=[O:6])#[N:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 521437Butanoic acid, 2-ethyl-2-methyl-, methyl ester

Product 1

HCID 159096Hexanenitrile, 4-ethyl-4-methyl-3-oxo-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 16.5 Kg portion of methyl 2-ethylbutyrate was reacted with 60 Kg of n-butyl lithium, diisopropylamine, and 19.1 Kg of methyl iodide to provide 17.4 Kg of methyl 2-ethyl-2-methylbutyrate. A 7.5 Kg portion of the ester thus formed was reacted with 3.25 Kg of acetonitrile and 5.03 g of sodium hydride in 33 liters of tetrahydrofuran to provide 1-ethyl-1-methylpropyl cyanomethyl ketone. The ketone thus formed was reacted with 4.35 Kg of hydroxylamine hydrochloride and 2.54 Kg of sodium hydroxide in 44 liters of water to provide 5.65 Kg of 5-amino-3-(1-ethyl-1-methylpropyl)isoxazole.

Sources & evidence

ORD record
ord-a05f8d7a3b964191acd61b19eeda8b5a
Source dataset
uspto-grants-1990_07
Patent number
US04943634

Reaction notes

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