Water → HCID 22033144, compound

HRID 1792368Notes

Reaction equation

HRID 1792368 reaction equation
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:3][CH2:4][CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].[Br:24][CH:25](Br)[CH3:26].O>C(COC)OC>[Br:24][CH2:25][CH2:26][C:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:1])[C:17]([F:18])([F:19])[F:20])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 112011,1-DibromoethaneHCID 24758Sodium hydrideHCID 12017062Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate

Product 1

HCID 22033144HCID 22033144, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Diethyl 2-(4,4,5,5,5-pentafluoropentyl)propane-1,3-dioate (51 0 mg, 1.592 mmol) was dissolved in anhydrous dimethoxyethane (5 ml). Sodium hydride (60%. 88 mg, 2.2 mmol) was added to the solution and then stirred at room temperature for 1 h under nitrogen atmosphere. Dibromoethane (0.82 ml, 9.55 mmol) was added to the mixture and then stirred at 70° C. for 5 h under nitrogen atmosphere. When the reaction was completed, the mixture was cooled to room temperature. Water was added to reaction solution which was then extracted with ethyl acetate. The extracted organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to column chromatography (n-hexane:dichloromethane=3:1) to obtain 489 mg (yield: 72° C.) of the title compound as a colorless oil.

Workup

  1. stirringstirred at 70° C. for 5 h under nitrogen atmosphere
  2. temperaturethe mixture was cooled to room temperature
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe extracted organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7af65a5ad4c44dc39c3e66abdfe7ff09
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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