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

HRID 980094Notes

Reaction equation

HRID 980094 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-6ed1e15bfa5742288deec1d7011955f6
Source dataset
uspto-grants-1987_01
Patent number
US04636243

Reaction notes

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