1-(2-Hydroxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol → 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

HRID 892503Notes

Reaction equation

HRID 892503 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)(O)[CH:9]=[C:10]([CH3:12])[CH3:11]>COCCOCCOC>[CH3:11][C:10]1([CH3:12])[CH:9]=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1]1

Participants

3

Reactant 1

HCID 198956121-(2-Hydroxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol

Product 1

HCID 187551522,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyranYield 58.4%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

4.42 g of 1-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol were dissolved in 70 ml of diethylene glycol dimethyl ether and heated at 150° C. for 2 hours. The mixture was allowed to cool to room temperature, the solvent was removed by evaporation and the residue was partitioned between ethyl acetate and sodium chloride solution. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution to give 2.4 g of 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran of melting point 80°-82° C.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed by evaporation
  3. customthe residue was partitioned between ethyl acetate and sodium chloride solution
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-6d07d9c9588247f099ec5dd0127aaac0
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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