Water → HCID 54326898, compound

HRID 1742011Notes

Reaction equation

HRID 1742011 reaction equation
[H-].[Na+].[CH:3](/[C:11]1[NH:12][CH:13]=[CH:14][CH:15]=1)=[CH:4]\[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH2:17][C:18]([O:20][CH3:21])=[O:19].O>CN(C)C=O>[CH:3]([C:11]1[N:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=1)=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 13451143HCID 13451143, compound

Product 1

HCID 54326898HCID 54326898, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (0.3 g, 0.0063 mol) was washed with petrol 60°-80° and suspended in dimethylformamide (DMF, 25 ml). The (E)-2-styrylpyrrole (1.0 g, 0.006 mol) in DMF (10 ml) was added dropwise at room temperature. After stirring for 11/2 hours, methyl bromoacetate (0.56 ml, 0.006 mol) in DMF (5 ml) was added dropwise. After 16 hours it was poured into water (200 ml) and extracted with ether (3×100 ml). The extracts were washed with brine dried and evaporated under reduced pressure to give a brown oil. Purification by column chromatography using silica gel with ethyl acetate: petrol 60°-80°, (1:1) as the eluent gave methyl (2-styrylpyrrol-1-yl)acetate (0.5 g, 30% yield) as a buff amorphous solid.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ether (3×100 ml)
  3. washThe extracts were washed with brine
  4. customdried
  5. customevaporated under reduced pressure
  6. customto give a brown oil
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-6f9cbd37730140158c8700281fd14c89
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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