Sodium Methoxide → HCID 19050669, compound

HRID 863745Notes

Reaction equation

HRID 863745 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°-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

Sources & evidence

ORD record
ord-4fdb6a6dae294a07a4648fa2f0959f51
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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