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

HRID 1958863Notes

Reaction equation

HRID 1958863 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:22])[C:8]=1[O:23][CH3:24])(=O)=O.[C-:25]#[N:26].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[CH2:14][O:13][C:9]1[C:8]([O:23][CH3:24])=[C:7]([CH2:6][C:25]#[N:26])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 866570093-(2,6-Dimethylbenzyloxy)-2-methoxybenzyl methanesulfonate

Product 1

HCID 669593842-(3-(2,6-Dimethylbenzyloxy)-2-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 3-(2,6-dimethylbenzyloxy)-2-methoxybenzyl methanesulfonate (Step C, 8.8 g, 30.26 mmol) and NaCN (1.60 g, 32.6 mmol) in dry DMF (40 ml) was heated at 85° C. for 18 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), concentrated, and passed through short silica gel column using methylene chloride to give the title compound as a yellow solid.

Workup

  1. temperaturethen cooled
  2. washThe organic layer was washed with water (30 ml)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a69f18c5f88548519e873ae801e9f88d
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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