Benzyl Bromide → HCID 12089327, compound

HRID 398370Notes

Reaction equation

HRID 398370 reaction equation
[OH:1][C:2]1[C:3](=[O:14])[NH:4][C:5]([CH3:13])=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:1][C:2]1[C:3](=[O:14])[NH:4][C:5]([CH3:13])=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 10796Cesium carbonateHCID 54725783HCID 54725783, compound

Product 1

HCID 12089327HCID 12089327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 3-hydroxy-4-ethoxycarbonyl-6-methyl-2-pyridinone (prepared by the method of Feist et al., Chem. Ber., 1902, vol. 35, p. 1545; 23.9 g, 121 mmol) and benzyl bromide (14.4 mL, 121 mmol) in DMF (400 mL) at 0° C. was added cesium carbonate (39.7, 121 mmol). The resulting mixture was stirred at 4° C. for 48 h. More benzyl bromide was added (2.8 mL, 24 mmol) and the mixture was stirred at 4° C. for another 72 h. The solvent was removed in vacuo and the residue was suspended in CH2Cl2. The solids were removed by filtration and the filtrate solvent was removed in vacuo. The residue was purified by flash column chromatography using 1:3 EtOAc:hexanes as eluant to give the title compound (18 g; HPLC RT=15.04 min, method B).

Workup

  1. stirringthe mixture was stirred at 4° C. for another 72 h
  2. customThe solvent was removed in vacuo
  3. customThe solids were removed by filtration
  4. customthe filtrate solvent was removed in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f8c6ae7a81a2409292b8afbe5b6b7f63
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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