HCID 19895618, compound → HCID 19895692, compound

HRID 892511Notes

Reaction equation

HRID 892511 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[C:19]([CH3:20])=[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[C:19]([CH3:20])=[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 19895618HCID 19895618, compound

Product 1

HCID 19895692HCID 19895692, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

4.5 g of 1-(2-hydroxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol were dissolved in 50 ml of diethylene glycol dimethyl ether and heated at reflux for 1 hour. The mixture was allowed to cool to room temperature and then evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) and then ethyl acetate/petroleum ether (1:2) for the elution to give 2.97 g of 2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran in the form of an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washethyl acetate/petroleum ether (1:2) for the elution

Sources & evidence

ORD record
ord-61ae6c30b5a54fcfb3d6e54f7e66eec6
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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