Ethylene Oxide → 2-(3-Bromofuran-2-yl)ethan-1-ol

HRID 1778361Notes

Reaction equation

HRID 1778361 reaction equation
C([Li])CCC.Br[C:7]1[O:8][CH:9]=[CH:10][C:11]=1[Br:12].[CH2:13]1[O:15][CH2:14]1.[Cl-].[NH4+]>C(OCC)C>[Br:12][C:11]1[CH:10]=[CH:9][O:8][C:7]=1[CH2:13][CH2:14][OH:15]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 70215012,3-DibromofuranHCID 178418339Butyllithium

Product 1

HCID 639438362-(3-Bromofuran-2-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.5M in hexanes, 12.9 mL) was added to a solution of 2,3-dibromofuran (6.63 g) in diethyl ether (40 mL) at −78° C. under nitrogen and the mixture was stirred for 15 minutes. A solution of ethylene oxide (15 mL) in diethyl ether (40 mL) was then added. The reaction mixture was stirred for a further 10 minutes then warmed to room temperature and stirred for 30 minutes. Saturated aqueous ammonium chloride was added and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25% to give 2-(3-bromofuran-2-yl)-ethanol (3.81 g) as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for a further 10 minutes
  2. stirringstirred for 30 minutes
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25%

Sources & evidence

ORD record
ord-e667d715e50049f897f234b06872a3b6
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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