Thionyl Chloride → HCID 12235031, compound

HRID 506146Notes

Reaction equation

HRID 506146 reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].S(Cl)(Cl)=O.[C:11]([O:15][C:16](=[O:20])CC#N)([CH3:14])([CH3:13])[CH3:12].[H-].[Na+]>C1COCC1.C(O)(=O)C>[C:11]([O:15][C:16](=[O:20])[CH:3]([C:4]#[N:5])[C:2](=[O:1])[CH3:6])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 70693tert-Butyl cyanoacetate2×HCID 755793-Oxobutyronitrile

Product 1

HCID 12235031HCID 12235031, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Scheme 2 below shows an alternative procedure for the preparation of 3-oxo-butyronitrile ii. This alternative procedure involves conversion of acetic acid vi to the corresponding acid chloride by reaction with a chlorinating agent such as thionyl chloride (SOCl2) followed by reaction of the anion of tert-butylcyanoacetate prepared by reaction of tert-butylcyanoacetate with a base such as sodium hydride (NaH) in a solvent such as THF to give 2-cyano-3-oxo-butanoic acid tert-butyl ester vii, which undergoes deprotection of the ester and decarboxylation to give 3-oxo-butyronitrile ii by reaction with an acid such as trifluoroacetic acid (TFA).

Sources & evidence

ORD record
ord-cf39724923c646748cf5b37a803313ca
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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