Ethylene Glycol → HCID 68461234, compound

HRID 499670Notes

Reaction equation

HRID 499670 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]Cl)[CH:10]=1.O>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][O:3][CH2:2][CH2:1][OH:4])[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chloride2×

Product 1

HCID 68461234HCID 68461234, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene glycol (0.084 mL, 1.51 mmol) was added to NaH (38 mg, 1.5 mmol, 95% in oil) in THF (3 mL). 3-(Chloromethyl)phenyl methyl ether (0.21 mL, 1.5 mmol) was added to the reaction, and the residual 3-(Chloromethyl)phenyl methyl ether was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was then added, and the reaction was heated at 60° C. for 18 h and then rt for 4 h. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (1×1 mL), and the combined organic layers were concentrated. The crude product was purified by flash chromatography eluting with 30% EtOAc/hexanes at 5 mL/min (10 mL) to give the title compound (114 mg, 42%). 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 (1×1 mL)
  3. concentrationthe combined organic layers were concentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 30% EtOAc/hexanes at 5 mL/min (10 mL)

Sources & evidence

ORD record
ord-02239215fcb844f8aa8b4221c32eb33a
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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