Allyl bromide → HCID 58333155, compound

HRID 2405067Notes

Reaction equation

HRID 2405067 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]([OH:12])([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH2:7])[CH3:2].[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4](=[O:13])[C:5]([O:12][CH2:18][CH:17]=[CH2:16])([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH2:7])[CH3:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 58333148HCID 58333148, compound

Product 1

HCID 58333155HCID 58333155, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-2-trifluoromethyl-but-3-enoic acid ethyl ester (3.6 g) in THF (100 mL) at 0° C. was added sodium hydride (1.1 g of 60% in oil), followed by addition of allyl bromide (2.3 mL) and tetrabutyl ammonium iodide (1.35 g). The resulting mixture was then heated to reflux for 5 h. The reaction was carefully quenched with NH4Cl (aq), extracted with EtOAc, and dried over Na2SO4. After concentration, the resulting crude material was filtered through a plug of silica gel and rinsed with 20% CH2Cl2/hexanes, then concentrated to yield the title compound as a yellow oil.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureto reflux for 5 h
  3. customThe reaction was carefully quenched with NH4Cl (aq)
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. filtrationthe resulting crude material was filtered through a plug of silica gel
  8. washrinsed with 20% CH2Cl2/hexanes
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2897ddcc4eda41a496497019166e2924
Source dataset
uspto-grants-2014_08
Patent number
US08802865B2

Reaction notes

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