Potassium Carbonate → 2-Methyl-6-{4-[1-(2-methoxyphenyl)-1-hydroxypropyl]-phenoxymethyl}-pyridine

HRID 745222Notes

Reaction equation

HRID 745222 reaction equation
[CH2:1]([C:3]([OH:19])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[N:28]=1>CC(CC(C)C)=O>[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])([OH:19])[CH2:1][CH3:2])=[CH:9][CH:8]=2)[N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 765462-(Chloromethyl)-6-methylpyridineHCID 14727321alpha-Ethyl-alpha-(2-methoxyphenyl)-4-hydroxy-benzylalcohol

Product 1

HCID 138824102-Methyl-6-{4-[1-(2-methoxyphenyl)-1-hydroxypropyl]-phenoxymethyl}-pyridine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

7.8 g of α-ethyl-α-(2-methoxyphenyl)-4-hydroxybenzyl-alcohol are dissolved in 65 ml. of methylisobutyl ketone, 9.1 g. of anhydrous potassium carbonate are added, and the reaction mixture is brought up to a boil. Thereafter, a solution of 4.7 g. of 2-methyl-6-chloromethyl-pyridine in 20 ml. of methylisobutyl ketone is added dropwise, and the reaction mixture is slightly boiled for 4 additional hours. After cooling, the reaction mixture is filtered off, and the filtrate is evaporated under reduced pressure. The residue is dissolved in benzene, the solution is washed with a 5% aqueous potassium hydroxide solution and then with water, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The crude product is crystallized from a mixture of ethyl acetate and cyclohexane. Melting point: 110° to 111° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in benzene
  5. washthe solution is washed with a 5% aqueous potassium hydroxide solution
  6. dry with materialwith water, dried over anhydrous magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customThe crude product is crystallized from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-bfec0704f9c74ef983dab14f0e5e9b82
Source dataset
uspto-grants-1986_07
Patent number
US04598080

Reaction notes

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