Ethyl Acetate → HCID 86674515, compound

HRID 869704Notes

Reaction equation

HRID 869704 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[CH2:12][CH2:11][CH2:10][O:9][C:6]2=[N:7][CH:8]=1.[Br:13]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C)C=O>[Br:13][C:8]1[N:7]=[C:6]2[O:9][CH2:10][CH2:11][CH2:12][C:5]2=[N:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 14166041HCID 14166041, compound

Product 1

HCID 86674515HCID 86674515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methoxy-6,7-dihydro-8H-pyrano[2,3-b]pyrazine (J. Chem. Soc. Perkin Trans. I 1988, 2585-2593; 3.16 g, 19.0 mmol) in N,N-dimethylformamide (95 mL) was added N-bromosuccinimide (5.08 g, 28.5 mmol) at room temperature, and then heated at 60° C. for 5 h. After being cooled to ambient temperature, the reaction mixture was diluted ethyl acetate, washed with 2% aqueous sodium sulfite, water, and saturated brine. The organic layer was dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give 3-bromo-2-methoxy-7,8-dihydro-6H-pyrano[2,3-b]pyrazine. MS (APCI): m/z 247 (M+H).

Workup

  1. temperatureAfter being cooled to ambient temperature
  2. washwashed with 2% aqueous sodium sulfite, water, and saturated brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Sources & evidence

ORD record
ord-8fee000e929243498677c9df1de6d68d
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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