Allyl bromide → HCID 67343897, compound

HRID 1669384Notes

Reaction equation

HRID 1669384 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:26])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:15]=1.[OH-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>CN(C)C=O>[CH2:31]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:26])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:15]=1)[CH:30]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 136344252HCID 136344252, compound

Product 1

HCID 67343897HCID 67343897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.71 g of 4-hydroxy-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 5 ml of dimethylformamide was added 0.09 g of sodium hydroxide (60% oily), and this was stirred at room temperature for 1 hour. 0.26 ml of allyl bromide was added, and this was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, 5 ml of tetrahydrofuran was added, insolubles were filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.30 g of 4-allyloxy-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (1b)] as a pale yellow crystal.

Workup

  1. stirringthis was stirred at room temperature overnight
  2. distillationThe solvent was distilled off under reduced pressure, 5 ml of tetrahydrofuran
  3. additionwas added
  4. filtrationinsolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38ce46544811402490c4206356c858d2
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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