Ethylene Glycol → 1-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-1H-pyrazole

HRID 2064920

反応式

HRID 2064920 の反応式
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4].[CH2:20](O)[CH2:21][OH:22].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CC(=O)OCC.O>[CH3:18][C:17]1([C:15]2[O:16][C:12]([CH2:11][N:9]3[CH:10]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[N:8]3)=[CH:13][CH:14]=2)[O:22][CH2:21][CH2:20][O:19]1

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 669282261-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanone

生成物 1

HCID 669285641-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-1H-pyrazole

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus under inert atmosphere (N2), a solution of 1-[5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanone (3.40 g, 14.46 mmol), ethylene glycol (8.1 mL, 144.84 mmol) and TsOH (28 mg, 0.15 mmol) in toluene (150.0 mL) was heated to reflux for 4 h. The reaction mixture was allowed to cool to rt. Water (200 mL) and EA (40 mL) were added and the aq. phase was extracted with EA (2×80 mL). The combined org. extracts were washed with sat. aq. NaHCO3 (200 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound as a yellow oil. TLC: rf (60:40 hept-EA)=0.31. LC-MS-conditions 02: tR=0.91 min. 1H NMR (400 MHz, CDCl3) δ 1.72 (s, 3H), 3.99 (dd, J=4.5, 2.5 Hz, 2H), 4.06 (dd, J=4.4, 2.5 Hz, 2H), 5.31 (s, 2H), 6.35 (d, J=3.3 Hz, 1H), 6.42 (d, J=3.3 Hz, 1H), 8.09 (s, 1H), 8.12 (s, 1H).

後処理

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureto reflux for 4 h
  3. extractionthe aq. phase was extracted with EA (2×80 mL)
  4. washextracts were washed with sat. aq. NaHCO3 (200 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (60:40 hept-EA)

出典と根拠

ORDレコード
ord-44f2dc82ef9e477cbe6fce0d2819cdf2
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

関連ノート

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