2-Hydroxy-2-methyl-propionitrile

Synonyms/Trade Names Cyanohydrin-2-propanone, 2-Cyano-2-propanol, a-Hydroxyisobutyronitrile, 2-Hydroxy-2-methyl-propionitrile, 2-Methyllactonitrile ... 

Reduction of 3-benzyl-8-chloro-4-oxo-4//-pyrido[l,2- ]pyrimidine-2-carboxylate <2004W004/064741> and 2-methyl-4-oxo-4//-pyrido[l,2-tf]pyrimidine-3-carboxylate <2003T4123> with DIBAL-H afforded 2- and 3-formyl derivatives, respectively. Reduction of /V-(4-fluorobenzyl)-3-hydroxy-8-[methoxy(methyl)amino]-4-oxo-6,7,8,9-tetra-hydro-4//-pyrido[l,2- ]pyrimidine-2-carboxamide with Zn-dust in aqueous AcOH afforded the 8-methylamino derivative, which was acylated with AcOH in the presence of Hiinig s base, HOBt, and l-(3-dimethylaminopro-pyl)-3-ethylcarbodiimide-HCl <2004W004/058756>. 3-(Perhydropyrido[l,2- ]pyrimidin-2-yl)propylamine was obtained by catalytic hydrogenation of 2-(perhydropyrido[l,2- ]pyrimidin-2-yl)propionitrile over a Pt02 catalyst <2003FRP1275647>. 

Hydroxy-4-methyl-4-penten-2-one (1) was prepared from 3-chloro-mesityl oxide using a modified procedure from the literature [ref.4], A reference sample of 4-methyl-4-penten-2,3-dione (2) was prepared from using the copper acetate method [ref.2], 4-methyl-pentan-2,3-dione (3) was purchased from Wiley Co. 2-Hydroxy-4-methyl-4-penten-3-one (4) was synthesized in 30% yield from 2-propenyl-magnesium bromide and 2-hydroxy-propionitrile in tetrahydrofurane. The structures of all compounds were confirmed by H-. C-NMR- and mass spectroscopy [ref. 5],... 

Propionitrile, 2,2 -azobis (2-methyl). See 2,2 -Azobisisobutyronitrile Propionitrile, 2-hydroxy-. See Lactonitrile Propionitrile, 3-methoxy-. See3-Methoxypropionitrile Propionitrile, 3-(triethoxysilyl)-. See2-Cyanoethyltriethoxysilane P-Propionolactone. See p-Propiolactone Propionphenone. See Propiophenone Propionylbenzene. See Ethyl phenyl ketone Propiophenone... 

Acrylonitrile was reacted with an unmodified cobalt catalyst to produce fi-formyl-propionitrile, which in turn was selectively reduced to y-hydroxy-butyronitrile [64]. In contrast, the use of a Rh complex modified with P(OPh)3 afforded mainly a-formyl-butyronitrile, which is a starting material for the synthesis of the PMMA monomer methyl methacrylate [65]. Occasionally, trapping of the formed cyanopropionaldehyde as acetal proved advantageous [66]. 

Enantioselective Aldol Additions. The reagent undergoes Lewis acid-catalyzed Mukaiyama-type additions to aldehydes to give syn a-methyl- 8-hydroxy thioesters with good yields and remarkable enantioselectivities (eq l). Slow addition of the aldehyde (3—4.5 h) in propionitrile is necessary for high enantio-selectivity. ... 

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