Methyl iodide → Butanoic acid, 2-ethyl-2-methyl-, methyl ester

HRID 1649304

Reaction equation

[CH2:1]([CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].[CH2:10]([Li])CCC.C(NC(C)C)(C)C.CI>>[CH2:1]([C:3]([CH3:10])([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 7912Diisopropylamine

HCID 69951Methyl 2-ethylbutyrate

HCID 178418339Butyllithium

Product 1

HCID 521437Butanoic acid, 2-ethyl-2-methyl-, methyl ester

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-8657c26c44ec4522ba316620dafe3def
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04416683

Linked notes

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