Ethylene Glycol → 851859-50-2

HRID 533879Notes

Reaction equation

HRID 533879 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.O>C1COCC1.CCOC(C)=O>[F:15][C:11]1[CH:10]=[C:9]([CH2:8][O:3][CH2:2][CH2:1][OH:4])[CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromide

Product 1

HCID 23325086851859-50-2Yield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene glycol (0.1 mL, 1.79 mmol) was added to NaH (46 mg, 1.81 mmol, 95% in oil) in THF (5 mL). 1-(Bromomethyl)-3-fluorobenzene (0.22 mL, 1.79 mmol) was added to the reaction, and the reaction was heated at 60° C. for 5 days. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (3×1 mL), and the combined organic layers were washed with saturated NaCl (1×2 mL), dried (Na2SO4), and concentrated. The crude product was purified on a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: 30% EtOAc/hexanes (fractions 1,2), 50% EtOAc/hexanes (fraction 3), and 75% EtOAc/hexanes (fraction 4) to give the title compound (76.2 mg, 25%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

  1. customthe layers were separated via pipette
  2. extractionThe aqueous layer was extracted with EtOAc (3×1 mL)
  3. washthe combined organic layers were washed with saturated NaCl (1×2 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified on a SPE cartridge (5 g silica)
  7. washeluting with the following 10 mL fractions

Sources & evidence

ORD record
ord-b8a32c54b47f40f9ab47bd63ae0432c3
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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