Sodium hydride → Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate

HRID 845733Notes

Reaction equation

HRID 845733 reaction equation
[C:1]1([C:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)(O)[CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[OH:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24]>ClCCl.CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH2:9][O:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])[CH:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 88068Methyl 3-HydroxybenzoateHCID 127170961-Phenyl-1-(3-pyridyl)-2-propen-1-ol

Product 1

HCID 54074383Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoateYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Phorphorus pentachloride (3.0 g, 14.2 mmoles) was suspended in dichloromethane (4 ml). To the suspension was added dropwise a solution of 1-phenyl-1-(3-pyridyl)-2-propen-1-ol (2.0 g, 9.5 mmoles) in dichloromethane (20 ml) at 0° C., then the mixture was stirred for one hour at room temperature, followed by washing with water, saturated aqueous solution of sodium hydrogen carbonate in the order. The organic layer is dried (magnesium sulfate), and concentrated to about 20 ml at a temperature not exceeding 30° C. The solution was further dried with molecular sieves 4A. This solution was named as (a) solution. Separately, sodium hydride (400 mg, 10 mmoles) is suspended in dimethylformamide (5 ml). To the suspension was added dropwise methyl metahydroxybenzoate (1.37 g, 9.0 mmoles) dissolved in dimethylformamide (5 ml). The mixture was stirred for 30 minutes at 0° C., to which was added dropwise the (a) solution, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured in ice-water, which is subjected to extraction with ethyl acetate, washed with water and dried (magnesium sulfate), followed by removing the solvent by evaporation under reduced pressure. The residue was subjected to silica-gel column chromatography, using ether-ethyl acetate (7:3) as eluant to yield methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate (If-56) (3.0 g, 92%).

Workup

  1. washby washing with water, saturated aqueous solution of sodium hydrogen carbonate in the order
  2. dry with materialThe organic layer is dried (magnesium sulfate)
  3. concentrationconcentrated to about 20 ml at a temperature not
  4. customexceeding 30° C
  5. dry with materialThe solution was further dried with molecular sieves 4A
  6. stirringThe mixture was stirred for 30 minutes at 0° C., to which
  7. stirringby stirring at room temperature for 1.5 hours
  8. extractionwhich is subjected to extraction with ethyl acetate
  9. washwashed with water
  10. dry with materialdried (magnesium sulfate)
  11. customby removing the solvent
  12. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-bbc0334093124f22862bb6579672d496
Source dataset
uspto-grants-1988_07
Patent number
US04760068

Reaction notes

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