Water → HCID 22626821, compound

HRID 277903Notes

Reaction equation

HRID 277903 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH3:6].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1.O>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]([CH2:4][CH2:5][CH3:6])[C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 22626821HCID 22626821, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (55-65%, 1.44 g, 36 mmoles) and, after 30 minutes under stirring, 1-bromo-propane (4.46 g, 36 mmoles) were added to a solution of 3-methoxy-phenyl-acetonitrile (4.4 g, 30 mmoles) in anhydrous DMF (30 ml) under N2 at room temperature. After 1.5 hours the mixture was poured into water (200 ml), extracted 3 times with ethyl ether, anhydrified and brought to dryness to give a residue which was chromatographed (eluent: petrolatum, then petrolatum/ethyl ether 95:5) to give 4.2 g of the title compound (yield: 74%).

Workup

  1. extractionextracted 3 times with ethyl ether
  2. customto give a residue which
  3. customwas chromatographed (eluent

Sources & evidence

ORD record
ord-8b5cc2296353488da0064f7beaec0412
Source dataset
uspto-grants-2002_03
Patent number
US06358973B1

Reaction notes

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