Triethylamine → HCID 12894082, compound

HRID 1249778Notes

Reaction equation

HRID 1249778 reaction equation
[CH3:1][O:2][CH:3]1[O:8][CH2:7][C:6](=[O:9])[CH:5]=[CH:4]1.[Br:10]Br.C(N(CC)CC)C>C(Cl)Cl.C1(C)C=CC=CC=1>[Br:10][C:5]1[C:6](=[O:9])[CH2:7][O:8][CH:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 130117856-Methoxy-2H-pyran-3(6H)-one

Product 1

HCID 12894082HCID 12894082, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-methoxy-2H-pyran-3(6H)-one 12.8 (0.1 mole) in 40 ml CH2Cl2 at 0° C. was added 16.0 g (0.1 mole) of bromine in 10 ml of CH2Cl2. Then 14 ml of triethylamine was added dropwise at 0° C. and the reaction was allowed to warm to room temperature and stir for two hours. The reaction was then diluted with 200 ml of toluene. After filtration, the organic solution was then washed with 5% NaHCO3 and brine, dried with Na2SO4, filtered and concentrated to yield the crude product as light brown solid. Recrystallisation from ethyl acetate afforded the title compound (17 g, 82%) as a white crystalline solid. m.p. 74-75° C.

Workup

  1. filtrationAfter filtration
  2. washthe organic solution was then washed with 5% NaHCO3 and brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the crude product as light brown solid
  7. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e5909ed122b243a4b78f078a1df40818
Source dataset
uspto-grants-2002_01
Patent number
US06335353B1

Reaction notes

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