Water → Ethyl (E)-3-{2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-2-methyl-2-propenoate

HRID 228516Notes

Reaction equation

HRID 228516 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[N:26]=[CH:25][CH:24]=[C:23]2[O:32][C:33]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:34]=1[CH:35]=O.O>O1CCCC1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[N:26]=[CH:25][CH:24]=[C:23]2[O:32][C:33]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:34]=1/[CH:35]=[C:8](\[CH3:9])/[C:6]([O:5][CH2:4][CH3:3])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 230782792-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxybenzaldehyde

Product 1

HCID 57756436Ethyl (E)-3-{2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-2-methyl-2-propenoateYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60 wt % oil, 52 mg) was dissolved in anhydrous tetrahydrofuran (1 ml), and a solution (0.5 ml) of triethyl 2-phosphonopropionate (119 mg) in tetrahydrofuran was added dropwise thereto under an argon atmosphere at 0° C. The mixture was stirred at 0° C. for 30 min, and a solution (0.5 ml) of 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methoxybenzaldehyde (100 mg) in tetrahydrofuran was then added dropwise thereto. The reaction mixture was stirred at room temperature for one hr, and water (1 ml) was then added dropwise to stop the reaction. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel using ethyl acetate-hexane for development to give the title compound (64 mg, yield 50%).

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for one hr
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe ethyl acetate layer was then washed with water and saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c1d11725a11e4f25a0434308d21929c7
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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