Ethylene Oxide → 2-Ethyl-5-(2-hydroxyethyl)furan

HRID 723663

Reaction equation

HRID 723663 reaction equation
[Li]CCCC.[CH2:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)[CH3:7].[CH2:13]1[O:15][CH2:14]1.[NH4+].[Cl-]>C1COCC1>[CH2:6]([C:8]1[O:9][C:10]([CH2:13][CH2:14][OH:15])=[CH:11][CH:12]=1)[CH3:7]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 185542-EthylfuranHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 218749232-Ethyl-5-(2-hydroxyethyl)furanYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (2.5 M in hexane, 4.4 mL, 11 mmol) was added to a solution of 2-ethylfuran (1.05 mL, 10 mmol) in THF (10 mL) at −25° C. The solution was warmed to rt and stirred for 3 h. Ethylene oxide (0.75 mL) was added at −78° C. The reaction was stirred for 0.5 h at −15° C. and overnight at rt. Aqueous sat. NH4Cl was added and the mixture was extracted with ether (3×). The combined extracts were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 30% EtOAc/7o % hexane gave 1.12 g (8.02 mmol, 80.2%) of compound 245A as a yellow oil.

Workup

  1. stirringThe reaction was stirred for 0.5 h at −15° C. and overnight at rt
  2. extractionthe mixture was extracted with ether (3×)
  3. washThe combined extracts were washed with water (1×) and brine (1×)
  4. dry with materialdried over Na2SO4
  5. customPurification by flash chromatography on silica gel eluting with 30% EtOAc/7o % hexane

Sources & evidence

ORD record
ord-94a82f075d704ed7aaa6451e19d92108
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Linked notes

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