Furfuryl Alcohol → Ethyl fur-2-ylmethoxyacetate

HRID 379460Notes

Reaction equation

HRID 379460 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 invacuo 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 invacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-28cfddb69b8c4cc08c06a1cb47e7806f
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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