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

HRID 1779751ノート

反応式

HRID 1779751 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 92152Silver(II) oxide触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eff9cff50e924e058362933de8a3752b
出典データセット
uspto-grants-1997_05
特許番号
US05627286

反応ノート

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