Ethylene Glycol → 3-[(2-Hydroxyethoxy)methyl]benzonitrile

HRID 916828Notes

Reaction equation

HRID 916828 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[C:7]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br)#[N:8]>CN(C=O)C>[OH:3][CH2:2][CH2:1][O:4][CH2:12][C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrileYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethylene glycol (7.5 g) in DMF (50 ml) under nitrogen at 0° C. was treated portionwise with sodium hydride (1.35 g) and stirred for 0.5 h. 3-Cyanobenzylbromide (4.74 g) was then added and the solution was allowed to warm to room temperature and stirred for 4 h. The solution was then concentrated in vacuo to remove the DMF. The residue was taken up in EtOAc, washed with phosphate buffer (pH=6.5) and water, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography (Biotage, 2×90 g) eluting with 40-60° C. petroleum ether-EtOAc (1:1) to give the title compound (2.62 g). LCMS RT=2.07 min.

Workup

  1. stirringstirred for 4 h
  2. concentrationThe solution was then concentrated in vacuo
  3. customto remove the DMF
  4. washwashed with phosphate buffer (pH=6.5) and water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by chromatography (Biotage, 2×90 g)
  8. washeluting with 40-60° C. petroleum ether-EtOAc (1:1)

Sources & evidence

ORD record
ord-507c7ada11894a70838e8fb6b975c84b
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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