Hydrochloric Acid → HCID 19927423, compound

HRID 1729156Notes

Reaction equation

HRID 1729156 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[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3O)[N:4]=1.[CH:23]([Mg]Cl)=[CH2:24].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3[CH:23]=[CH2:24])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199274177-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalideHCID 178461836HCID 178461836, compound2×

Product 1

HCID 19927423HCID 19927423, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.6 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide (see Example 84) are placed in 60 ml of absolute tetrahydrofuran at -45° C., and the solution is treated within 10 minutes with 18 ml of a 2M solution of vinylmagnesium chloride solution in tetrahydrofuran. The reaction solution is then stirred for approximately 16 hours at room temperature, a further 6 ml of vinyl-magnesium chloride solution are added and the reaction solution is heated at reflux temperature for a further hour. When it has cooled, the reaction solution is acidified with 1N hydrochloric acid and freed of tetrahydrofuran in a rotary evaporator. The aqueous phase is then extracted with tert-butyl methyl ether, and the organic phase is washed and concentrated by evaporation under reduced pressure. Silica gel chromatography using ethyl acetate/n-hexane (2:3) as eluant yields pure 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-vinyl-phthalide, m.p. 94°-97° C.

Workup

  1. temperaturethe reaction solution is heated
  2. temperatureat reflux temperature for a further hour
  3. temperatureWhen it has cooled
  4. customfreed of tetrahydrofuran in a rotary evaporator
  5. extractionThe aqueous phase is then extracted with tert-butyl methyl ether
  6. washthe organic phase is washed
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-537b8b26e9df40a3a93560871227600f
Source dataset
uspto-grants-1994_07
Patent number
US05332717

Reaction notes

Loading…