Sodium Methoxide → HCID 19050669, compound

HRID 1779300Notes

Reaction equation

HRID 1779300 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][C:7]2(C#N)[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1.[CH3:24][O-:25].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][C:7]2([O:25][CH3:24])[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 19050667HCID 19050667, compound

Product 1

HCID 19050669HCID 19050669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of 7-chloro-3-cyano-3-(4,6-dimethoxy-2-pyrimidinyl)phthalide is slurried in 20 ml of methanol and the solution cooled with ice and 0.6 ml of sodium methoxide added dropwise. After stirring for 10 min a further 1 ml of sodium methoxide is added and stirring continued for 10 min and the mixture is then quenched with 2N H2SO4. Methanol is removed on a rotovaporator and the residue partitioned between water and ethyl acetate. The organic phase is dried over Na2SO4 and concentrated. Flash chromatography of the residue over silica gel using 25% ethyl acetate/hexane yields a white solid m.p. 180°14 183° C.

Workup

  1. additionadded dropwise
  2. additionis added
  3. customthe mixture is then quenched with 2N H2SO4
  4. customMethanol is removed on a rotovaporator
  5. customthe residue partitioned between water and ethyl acetate
  6. dry with materialThe organic phase is dried over Na2SO4
  7. concentrationconcentrated
  8. customFlash chromatography of the residue over silica gel using 25% ethyl acetate/hexane yields a white solid m.p. 180°14 183° C.

Sources & evidence

ORD record
ord-0ac41b3470874ff8b1e194e2ebbd7b3f
Source dataset
uspto-grants-1997_05
Patent number
US05627137

Reaction notes

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