Dimethyl Sulfoxide → 2-(2-Benzyloxy-5-methoxymethoxyphenyl)acetonitrile

HRID 1294105Notes

Reaction equation

HRID 1294105 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.[C-:25]#[N:26].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19][C:25]#[N:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 178613821-Benzyloxy-2-bromomethyl-4-methoxymethoxybenzene

Product 1

HCID 178612212-(2-Benzyloxy-5-methoxymethoxyphenyl)acetonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-benzyloxy-2-bromomethyl-4-methoxymethoxybenzene (0.30 g) and dimethyl sulfoxide (3 mL) was added an aqueous solution (0.3 mL) of sodium cyanide (0.05 g) at room temperature and the mixture was stirred for 13 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 2-(2-benzyloxy-5-methoxymethoxyphenyl)acetonitrile as a colorless oil (0.23 g, 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c75d7b2d12ad45738cc1141e25a6f6a1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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