Sodium Iodide → 5-p-Methoxybenzyloxy-2-methyl-4-pyrone

HRID 1461239Notes

Reaction equation

HRID 1461239 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]Cl)[O:13][CH:14]=2)=[CH:5][CH:4]=1.[I-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH3:15])[O:13][CH:14]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 199802145-p-Methoxybenzyloxy-2-chloromethyl-4-pyrone

Product 1

HCID 199802165-p-Methoxybenzyloxy-2-methyl-4-pyrone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-p-Methoxybenzyloxy-2-chloromethyl-4-pyrone, 10 g, was dissolved in 100 ml of acetone and, 5.5 g of sodium iodide and 11.6 g of triphenylphosphine were added to the solution followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction liquid was concentrated to dryness and the residue was added to 50 ml of water and 100 ml of dichloromethane. Under ice cooling, the pH was adjusted to 7.0 with saturated sodium hydrogencarbonate aqueous solution and the mixture was stirred at the same temperature for 30 minutes. The organic phase was washed with 20 ml of water. After drying over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (500 g) to give 8.2 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated to dryness
  4. additionthe residue was added to 50 ml of water and 100 ml of dichloromethane
  5. stirringthe mixture was stirred at the same temperature for 30 minutes
  6. washThe organic phase was washed with 20 ml of water
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. concentrationthe organic phase was concentrated under reduced pressure
  9. custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-c19f286fec2d4a098747fc5498b4a38a
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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