Sodium Methoxide → HCID 15377780, compound

HRID 1079282Notes

Reaction equation

HRID 1079282 reaction equation
[CH2:1]([O:5][C:6]1[C:11]2[CH:12]=[CH:13][C:14]([O:16]C(=O)C)=[CH:15][C:10]=2[O:9][C:8](=[O:20])[C:7]=1[O:21][C:22](=[O:24])[CH3:23])[CH2:2][CH2:3][CH3:4].C[O-].[Na+]>CO>[C:22]([O:21][C:7]1[C:8](=[O:20])[O:9][C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=2[C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 23366471HCID 23366471, compound

Product 1

HCID 15377780HCID 15377780, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 17.31 g of 4-butoxy-3, 7-diacetoxy-2H-l-benzopyran-2-one (51.79 mmol) in 170 ml of methanol was added 2.66 g of sodium methoxide (49.20 mmol) and the reaction mixture was stirred at room temperature for 3 hours. Then 22.36 g of Amberlyst-15 was added, and the mixture was stirred at room temperature for 1 hour. Amberlyst-15 was filtered off and the filtrate was concentrated under reduced pressure to give a crystalline product. The product was reprecipitated from tertahydrofuran and hexane to give 12.87 g of the title compound. (yield=85%)

Workup

  1. additionThen 22.36 g of Amberlyst-15 was added
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationAmberlyst-15 was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give a crystalline product
  6. customThe product was reprecipitated from tertahydrofuran and hexane

Sources & evidence

ORD record
ord-7562b3561b1a410caa8564ca15ef695d
Source dataset
uspto-grants-1996_12
Patent number
US05580552

Reaction notes

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