Potassium Carbonate → HCID 66959086, compound

HRID 337258Notes

Reaction equation

HRID 337258 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21]Cl>CN(C=O)C.CCOC(C)=O>[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 18440061HCID 18440061, compound

Product 1

HCID 66959086HCID 66959086, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-Hydroxy-4-methylphenyl)acetonitrile (Step A, 2.18 g, 14.8 mmol), K2CO3 (2.66 g, 19.2 mmol) in dry DMF (20 ml) was added 2,6-Dimethylbenzyl chloride (2.97 g, 19.2 mmol) at room temperature under argon. The reaction mixture was stirred for 16 hours, diluted with EtOAc (40 ml), washed with water (20 ml) and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound as a white solid.

Workup

  1. washwashed with water (20 ml) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Sources & evidence

ORD record
ord-266f456e38fa4eac88f404e48577250d
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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