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Ethylene Glycol → 2-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2'-[1,3]dioxolane]

HRID 1891398
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HRID 1891398 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17](=[O:19])[CH2:18][CH:13]2[CH2:12]1.[CH2:20](O)[CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17]3([CH2:18][CH:13]2[CH2:12]1)[O:22][CH2:21][CH2:20][O:19]3
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참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 711829272-(2-Fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrol

생성물 1

HCID 711829442-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2'-[1,3]dioxolane]

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

19.74 g (74.7 mmol) of 2-(2-fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrol prepared in the step 3 and 5.0 ml (89.6 mmol) of ethylene glycol were dissolved in 200 ml of benzene, 1.00 g (5.2 mmol) of p-toluene sulfonic acid hydrate was added, and the mixture was heated to reflux for 1 hour while removing generated water. After the reaction was completed, the mixture was washed with a saturated aqueous solution of sodium carbonate and water, and then, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound, of which NMR data is as follow.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customwhile removing
  4. washthe mixture was washed with a saturated aqueous solution of sodium carbonate and water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c0e85634b9594580ae8953478809e123
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507540B2

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