3-Methyl-2-buten-1-OL → 2-[[(3-Methyl-2-butenyl)oxy]methyl]-5-nitrofuran

HRID 1779751Notes

Reaction equation

HRID 1779751 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[CH:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[O:9][C:8]=1[CH2:15]Br.C[C]C>[Ag]=O>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][O:5][CH2:15][C:8]1[O:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][CH:7]=1

Participants

5

Reactant 3

HCID 111733-Methyl-2-buten-1-OLHCID 7198242-(Bromomethyl)-5-nitrofuranHCID 6432418Propan-2,2-diyl3×

Product 1

HCID 189291392-[[(3-Methyl-2-butenyl)oxy]methyl]-5-nitrofuran

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

Freshly prepared silver oxide (34.8 g, 0.15 mol) was added to a mixture of 3-methyl-2-buten-1-ol (21.0 g, 25 mL, 0.24 mol) and 5-nitro-2-furfuryl bromide (18.8 g, 0.1 mol) and stirred at room temperature for 12 h. Silver salts were removed by filtration and the filter cake was washed with ether (200 mL). The filtrate and the washings were combined and evaporated to remove ether and excess 3-methyl-2-buten-1-ol. The oil obtained was purified by column chromatography (silica gel, hexane:ethyl acetate, 7:1). Fractions containing the product were collected and evaporated to give a light yellow oil. Yield 5.5 g. 1H NMR (CDCl3) ε 1.69 and 1.77 (s, 6H, CH3), 4.09 [d, 2H, (CH3)2C=CHCH2 --OCH2)], 4.64 [s, 2H, (CH3)2C=CHCH2 --OCH2)], 5.38 (t, 1H, (CH3)2C=CH--), 6.6 and 7.27 (d, 2H, ArH).

Workup

  1. customSilver salts were removed by filtration
  2. washthe filter cake was washed with ether (200 mL)
  3. customevaporated
  4. customto remove ether and excess 3-methyl-2-buten-1-ol
  5. customThe oil obtained
  6. customwas purified by column chromatography (silica gel, hexane:ethyl acetate, 7:1)
  7. additionFractions containing the product
  8. customwere collected
  9. customevaporated
  10. customto give a light yellow oil

Sources & evidence

ORD record
ord-eff9cff50e924e058362933de8a3752b
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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