Triethylamine → Acetoxymethyl 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylate

HRID 1659502Notes

Reaction equation

HRID 1659502 reaction equation
[C:1]([O:4][CH2:5]Cl)(=[O:3])[CH3:2].[Br:7][C:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:10][C:9]=1[C:21]([OH:23])=[O:22].C(N(CC)CC)C>CN(C=O)C>[Br:7][C:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:10][C:9]=1[C:21]([O:23][CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69366Chloromethyl acetateHCID 155783753-Bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylic acid

Product 1

HCID 15578427Acetoxymethyl 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloromethyl acetate (2.2 ml) was added to a stirred solution of 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylic acid (5.9 g) and triethylamine (2.9 ml) in dry DMF (40 ml). The solution was heated at 70°-80° C. for 3 hours, then poured on to ice-water and extracted with ethyl acetate. The extract was washed with sodium bicarbonate solution, dried and evaporated, and the residue was crystallised from ethanol-water. The crude product was purified by chromatography on silica-gel and recrystallisation from ethyl acetate-petroleum ether 60°-80° C. gave the title product as white needles (mp 121° C.).

Workup

  1. temperatureThe solution was heated at 70°-80° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customthe residue was crystallised from ethanol-water
  7. customThe crude product was purified by chromatography on silica-gel and recrystallisation from ethyl acetate-petroleum ether 60°-80° C.

Sources & evidence

ORD record
ord-b2b95c1e980f4dbeb19ef4c61dfa3765
Source dataset
uspto-grants-1981_12
Patent number
US04304728

Reaction notes

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