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

HRID 1779751노트

반응식

HRID 1779751 반응식
[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

참가 물질

5

반응물 3

HCID 111733-Methyl-2-buten-1-OLHCID 7198242-(Bromomethyl)-5-nitrofuranHCID 6432418Propan-2,2-diyl3회

생성물 1

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

시약·촉매·용매 1

HCID 92152Silver(II) oxide촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eff9cff50e924e058362933de8a3752b
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627286

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