Sodium hydride → HCID 21094277, compound

HRID 1350069Notes

Reaction equation

HRID 1350069 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[H-].[Na+]>CN(C)C=O.O>[C:10]([CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 21094277HCID 21094277, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Two grams of (3-methoxyphenyl)acetonitrile and 1.5 ml of ethyl 4-bromobutyrate are dissolved in 50 ml of dimethylformamide at 0° C. Six hundred milligrams of 60% sodium hydride (600 mg; 15 mmol) are progressively added to the solution. The reaction mixture is stirred at ambient temperature for 4 hours, taken up in 100 ml of acidic water and extracted with ether. The organic phase is then dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oil obtained is purified on a column (eluant:ether/cyclohexane 4/6) to yield the title product in the form of a yellow oil.

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic phase is then dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe oil obtained
  6. customis purified on a column (eluant:ether/cyclohexane 4/6)

Sources & evidence

ORD record
ord-1f1659075bbf467abb49920bdc648e12
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

Loading…