Allyl bromide → HCID 20247677, compound

HRID 1589084Notes

Reaction equation

HRID 1589084 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:17]=2)=[C:12]([NH:26][CH3:27])[O:11]1.[CH2:28](Br)[CH:29]=C>O.C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:17]=2)=[C:12]([NH:26][CH2:27][CH:28]=[CH2:29])[O:11]1

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 20247655HCID 20247655, compound

Product 1

HCID 20247677HCID 20247677, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

One gram of sodium hydroxide in 4.0 ml of water is added to a mixture of 4.0 g of 2-(2-fluorophenyl)-3-oxo-4-(3-methoxycarbonylphenyl)-5-methylamino-2,3-dihydrofuran in 80 ml of methylene chloride at room temperature followed by the addition of 1.48 g of allyl bromide and 0.27 g of benzyltriethylammonium chloride. This will result in a two-phase mixture. This mixture is stirred at room temperature for about 18 hours and this is washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by chromatography over silica gel eluting with chloroform to yield the title compound.

Workup

  1. customThis will result in a two-phase mixture
  2. washthis is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography over silica gel eluting with chloroform

Sources & evidence

ORD record
ord-a8d4de0a0bb947d68f3101c5a092228a
Source dataset
uspto-grants-1986_02
Patent number
US04568377

Reaction notes

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