Water → 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic Acid

HRID 51999Notes

Reaction equation

HRID 51999 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:23]([C:24]([O:26]C)=[O:25])=[C:16]3[CH2:17][CH:18]([O:20][CH2:21][CH3:22])[O:19][C:15]3=[CH:14][CH:13]=2)[N:4]=1.[OH-].[Na+].O>CS(C)=O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:23]([C:24]([OH:26])=[O:25])=[C:16]3[CH2:17][CH:18]([O:20][CH2:21][CH3:22])[O:19][C:15]3=[CH:14][CH:13]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19962778Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate

Product 1

HCID 199627985-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

While stirring 1.2 g of methyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate in 20 ml of dimethylsulfoxide at room temperature, 2 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes and then the mixture was further stirred for 15 hours. The mixture was poured into water and extracted with diethyl ether. Then, the aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 1.0 g (yield: 87%) of the desired compound.

Workup

  1. extractionextracted with diethyl ether
  2. customprecipitated crystals
  3. extractionwere extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationIt was concentrated under reduced pressure
  7. customthe oily substance thereby obtained
  8. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-cb348105a1804da6a1f41638018584f6
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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