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

HRID 2417965Notes

Reaction equation

HRID 2417965 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 ethanolwater. 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 ethanolwater
  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-23c6e12793974417be005deb46eb3980
Source dataset
uspto-grants-1984_09
Patent number
US04471129

Reaction notes

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