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

HRID 2064920

반응식

HRID 2064920 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-44f2dc82ef9e477cbe6fce0d2819cdf2
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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