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

HRID 1534051Notes

Reaction equation

HRID 1534051 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-3b2cb6cc99ec401ea4ccc1b77ba48232
Source dataset
uspto-grants-1992_02
Patent number
US05086184

Reaction notes

Loading…