Furfuryl Alcohol → Ethyl fur-2-ylmethoxyacetate

HRID 2269869Notes

Reaction equation

HRID 2269869 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(OCC)(=O)C.ClCCl>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][O:7][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 7361Furfuryl AlcoholHCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 14746268Ethyl fur-2-ylmethoxyacetate

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Combine furfuryl alcohol (1 mL, 11.6 mmol) and tetrahydrofuran (20 mL). Add portionwise sodium hydride (0.57 g, 60% in oil, 14 mmol). After gas evolution ceases, add ethyl bromoacetate (1.3 mL, 11.7 mmol). Heat to reflux. After 2.5 hours cool to ambient temperature. After 18 hours, partition the reaction mixture between ethyl acetate and water. Separate the aqueous layer and extract twice with ethyl acetate. Combine the organic layers and extract with saturated aqueous sodium chloride solution, dry over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1% ethyl acetate/dichloromethane to give ethyl fur-2-ylmethoxyacetate: Rf=0.62 (silica gel, 5% ethyl acetate/dichloromethane).

Workup

  1. temperatureHeat to reflux
  2. custompartition the reaction mixture between ethyl acetate and water
  3. customSeparate the aqueous layer
  4. extractionextract twice with ethyl acetate
  5. extractionextract with saturated aqueous sodium chloride solution
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-f6ab3fbd2c5f4a6a962578c4e10ab001
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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