Tetrahydrofuran → Fur-2-ylmethyl 2-hydroxyethyl ether

HRID 2269870Notes

Reaction equation

HRID 2269870 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][CH2:8][C:9](OCC)=[O:10].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C.ClCCl.O>[OH:10][CH2:9][CH2:8][O:7][CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14746268Ethyl fur-2-ylmethoxyacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10103270Fur-2-ylmethyl 2-hydroxyethyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Combine ethyl 2-fur-2-ylmethoxyacetate (1.2 g, 6.5 mmol) and tetrahydrofuran (10 mL). Cool in an ice-bath. Add dropwise a solution of lithium aluminum hydride (8.0 mL, 1.0 M in THF, 8.0 mmol). After 2 hours, add water (0.3 mL), add 15% sodium hydroxide solution (0.3 mL), and add water (0.9 mL). Stir vigorously. After 15 minutes, filter the reaction mixture and dry the filtrate over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2% ethyl acetate/dichloromethane to give fur-2-ylmethyl 2-hydroxyethyl ether: Rf=0.22 (silica gel, 5% acetone/dichloromethane).

Workup

  1. temperatureCool in an ice-bath
  2. waitAfter 15 minutes
  3. filtrationfilter the reaction mixture
  4. dry with materialdry the filtrate over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-64083ef9b3fb498c9b8a9a7863d236bf
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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