Sodium Ethoxide http://reag.paperplane.io/00002518.

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Sodium Ethoxide1
NaOEt

[141-52-6] · C2H5NaO · Sodium Ethoxide · (MW 68.06)

(used as a base for the a-deprotonation of carbonyl-containing compounds for subsequent

intermolecular2 or intramolecular1f condensations, displacements,3 or skeletal
rearrangements,1d,4 arylacetonitriles,5 nitro-containing aliphatic compounds,6 sulfonium salts,3j,7
for the dehydration of carbinolamines8 and for dehydrohalogenation,1b,9 for the N-deprotonation
of amides,10a-d tosylamines,10e amine hydrochlorides1c or toluenesulfonates,10f cyanamide,10g
and the S-deprotonations of sulfides,1c,11 often followed by cyclizations;1c,10b,10g,11 can be used
as a nucleophile in ipso substitution reactions of vinyl sulfides,12a aromatic halides,12b-i
sometimes catalyzed by copper12c or palladium,12h,i aryl sulfones,12j and aromatic nitro
compounds,12k in the Williamson ether synthesis,13a-c in displacements of halo,13d-h nitro,13e
thiooxy,13g,h and phenoxy13g groups from dichloromethane and chloroform analogs, in a novel
transesterification-conjugate addition protocol of acrylic esters,14 with a-nitro epoxides to form
a-ethoxy ketones,15 in the nucleophilic attack on nitriles1e,16 and polyhaloalkenes,17 in reaction
with chlorodiphenylphosphine to form Arbuzov precursors,18 and with Grignard reagents to form
organomagnesium ethoxides19)

Physical Data: mp >300 °C.

Solubility: sol ethanol, diethyl ether.

Form Supplied in: white or yellowish powder or as 21 wt % solution in ethanol; widely available.

Preparative Methods: it is often necessary to prepare sodium ethoxide immediately prior to its
use. Preparation of a 6-10% solution in ethanol: to commercial absolute ethanol is added the
required amount of Sodium in lumps or slices with or without stirring and with or without a
nitrogen atmosphere and the solution is cooled or heated as required until the metal is dissolved.
The evolved hydrogen should be vented into a hood. Addition of ethanol to sodium is also
reported. Alcohol-free reagent can also be prepared.1a

Handling, Storage, and Precautions: is a hygroscopic, flammable, corrosive, and toxic solid
which will decompose upon exposure to air. The solid or solution reagent should be tightly sealed
under an inert atmosphere in a dark bottle.

General Discussion.

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