Benzyl Bromide → HCID 23366424, compound

HRID 1079280Notes

Reaction equation

HRID 1079280 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:18])[O:5][C:6]2[CH:13]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:10][C:7]=2[C:8]=1[OH:9].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4](=[O:18])[O:5][C:6]2[CH:13]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:10][C:7]=2[C:8]=1[O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 54693047HCID 54693047, compound

Product 1

HCID 23366424HCID 23366424, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8.11 g of 3-methoxy-4-hydroxy-7-acetoxy-2H-l-benzopyran-2-one (27.8 mmol) and 5.71 g of benzyl bromide (33.4mmol) in 50 ml of DMF was added 4.61 g of sodium carbonate (33.4 mmol) under argon atmosphere, then the mixture was stirred at 50° for 2 hours. The solid in the reaction mixture was filtered off, the filtrate was poured into 200 ml of water and extracted with 500 ml of benzene. The organic layler was concentrated in vacuo after drying over magnesium sulfate to give oily residue. The residue was purified on silica gel column chromatography (eluent: benzene/ethyl acetate=7/3) to give 3.50 g of the title compound. (yield=33%)

Workup

  1. filtrationThe solid in the reaction mixture was filtered off
  2. additionthe filtrate was poured into 200 ml of water
  3. extractionextracted with 500 ml of benzene
  4. concentrationThe organic layler was concentrated in vacuo
  5. dry with materialafter drying over magnesium sulfate
  6. customto give oily residue
  7. customThe residue was purified on silica gel column chromatography (eluent: benzene/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-46502d66193c4f6baf46b7f30526d85c
Source dataset
uspto-grants-1996_12
Patent number
US05580552

Reaction notes

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