Water → 4-(1,1-Dicyanoethyl)anisole

HRID 481509

Reaction equation

HRID 481509 reaction equation
[C:1]([CH:3]([C:12]#[N:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)#[N:2].[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[C:1]([C:3]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)([C:12]#[N:13])[CH3:16])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 641441(4-Methoxyphenyl)malononitrile

Product 1

HCID 190664454-(1,1-Dicyanoethyl)anisoleYield 268.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Compound 35 (1.0 g, 6.0 mmol) and NaH (280 mg, 7.0 mmol) in DMF (12 ml) was added MeI (1.0 g, 7.0 mmol) at room temperature. After the mixture was stirred for 22 hours, the mixture was poured into H2O (30 ml), and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated to give a yellow oil (3 g), which was purified by a column chromatography on silica gel to give Compound 35 as a colorless solid (900 mg, 81%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1f92e4c444b74b1aa93def5842cf23b9
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Linked notes

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