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

HRID 337271Notes

Reaction equation

HRID 337271 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-45703eaad18742aba5ac439a2ce77a44
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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