Methyl nitrite → 2-Hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile

HRID 48132

Reaction equation

HRID 48132 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH2:11][C:12]#[N:13])=[CH:5][CH:4]=1.[N:14](OC)=[O:15]>CO>[OH:15][N:14]=[C:11]([CH:10]=[CH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:12]#[N:13]

Participants

4

Reactant 2

HCID 12231Methyl nitriteHCID 544351994-(4-Methoxyphenyl)but-3-enenitrile

Product 1

HCID 867593582-Hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrileYield 35,606.699%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Methoxy-phenyl)-but-3-enenitrile (5.0 g; 0.025 mmol) dissolved in 90 ml of methanol is treated with ca 0.050 mol of gaseous methyl nitrite in the same way as described in example 2.2. After stirring overnight at ca 25° C., the reaction mixture is rotary evaporated and partitioned between 200 ml of 0.5 N HCl and 200 ml ethyl acetate. The aqueous phase is extracted with 50 ml of ethyl acetate. The combined organic extracts are evaporated and purified by flash chromatography (150 g SiO2; hexane:ethyl acetate 80:20 v:v); to yield 2-hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile 1.8 g (36%) as a yellow solid which is used for the next reaction without further purification.

Workup

  1. customthe reaction mixture is rotary evaporated
  2. custompartitioned between 200 ml of 0.5 N HCl and 200 ml ethyl acetate
  3. extractionThe aqueous phase is extracted with 50 ml of ethyl acetate
  4. customThe combined organic extracts are evaporated
  5. custompurified by flash chromatography (150 g SiO2; hexane:ethyl acetate 80:20 v:v)

Sources & evidence

ORD record
ord-ae3f0270cd1b41a78624777403f111f4
Source dataset
uspto-grants-2004_03
Patent number
US06703182B1

Linked notes

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