Sodium Cyanide → 2-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

HRID 1958845Notes

Reaction equation

HRID 1958845 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:9][C:10]1NN=N[N:11]=1.[C-]#N.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:9][C:10]#[N:11])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 1784899435-(3-(2,6-Dimethylbenzyloxy)-4-methoxybenzyl)-1H-tetrazole

Product 1

HCID 669590872-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 2-((5-(bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene (Step D, 3.28 g, 9.7 mmol) and NaCN (0.624 g, 12.7 mmol) in dry DMF (20 ml) was heated at 120° C. for 2.5 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), brine, dried over Na2SO2, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Workup

  1. temperaturethen cooled
  2. washThe organic layer was washed with water (30 ml), brine
  3. dry with materialdried over Na2SO2
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-a9d598ec38564ea59d2abc3510900e93
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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