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

HRID 51998Notes

Reaction equation

[CH2:1]([O:3][CH:4]1[CH2:8][C:7]2=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]([OH:13])=[CH:11][CH:12]=[C:6]2[O:5]1)[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22](S(C)(=O)=O)[N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([O:13][C:10]2[C:9]([C:14]([O:16][CH3:17])=[O:15])=[C:7]3[CH2:8][CH:4]([O:3][CH2:1][CH3:2])[O:5][C:6]3=[CH:12][CH:11]=2)[N:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture comprising 1.0 g of methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate, 1.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.78 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 100° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. 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=4/1) to obtain 1.5 g (yield: 95%) of the desired compound.

Workup

temperaturewas heated
customwas returned to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationIt was concentrated under reduced pressure
customthe oily substance thereby obtained
customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-877c567981af4e73ad343d16d8173690
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616537

Reaction notes

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