Water → 2-[2-[(6-Bromohexyl)oxy]ethyl]furan

HRID 359741Notes

Reaction equation

HRID 359741 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[H-].[Na+].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.O>CN(C=O)C>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:8][CH2:7][CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 6421102-Furanethanol

Product 1

HCID 199961002-[2-[(6-Bromohexyl)oxy]ethyl]furanYield 34.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Furanethanol (2 g) in DMF (5 ml) was added dropwise to a suspension of sodium hydride (0.43 g) in DMF (20 ml). The mixture was stirred for 30 min and added dropwise to 1,6-dibromohexane (21.8 g). The resulting suspension was heated at 60°-70° for 18 h, poured into water (200 ml) and extracted with diethyl ether (3×100 ml). The dried extract was evaporated and the residue was purified on a column of silica eluted with cyclohexane. The resulting oil was fractionally distilled (Kugelrohr) to give the title compound as a colourless oil (1.7 g) b.p. 75°-80°/0.3 Torr.

Workup

  1. temperatureThe resulting suspension was heated at 60°-70° for 18 h
  2. extractionextracted with diethyl ether (3×100 ml)
  3. extractionThe dried extract
  4. customwas evaporated
  5. customthe residue was purified on a column of silica
  6. washeluted with cyclohexane
  7. distillationThe resulting oil was fractionally distilled (Kugelrohr)

Sources & evidence

ORD record
ord-e8b3d7742c5140938f0956ebde551a51
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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