Glycidol → 2-(((4-Methoxyphenyl)methoxy)methyl)oxirane

HRID 2201222Notes

Reaction equation

HRID 2201222 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:13]1[O:15][CH:14]1[CH2:16][OH:17]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:17][CH2:16][CH:14]2[CH2:13][O:15]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 27740762-(((4-Methoxyphenyl)methoxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

p-Methoxybenzyl chloride (2.326 g, 14.85 mmol) was added slowly to a suspension of sodium hydride (60% dispersion in mineral oil, 0.594 g, 14.85 mmol) in DMF (25 mL) at 0° C. and the mixture stirred for 25 mins. Glycidol (1 g, 13.50 mmol) was then added dropwise over 25 mins, the mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was diluted with EtOAc (50 ml) and washed with saturated NH4Cl (aq) (30 ml), saturated NaHCO3 (aq) (50 ml) and brine (100 ml). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-10% EtOAc/hexane, afforded the title compound.

Workup

  1. stirringstirred for 3 days
  2. washwashed with saturated NH4Cl (aq) (30 ml), saturated NaHCO3 (aq) (50 ml) and brine (100 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 0-10% EtOAc/hexane

Sources & evidence

ORD record
ord-a8585a06f9004f9b8c10b5afdc8fe35a
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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