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1-Hexanol → {4-(4-Hexanoxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane

HRID 1391862
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HRID 1391862 반응식
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[F:10][C:11]1[C:16]([C:17]2[C:22]([F:23])=[C:21]([F:24])[C:20]([CH:25]([S:33]([C:36]([F:39])([F:38])[F:37])(=[O:35])=[O:34])[S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])=[C:19]([F:40])[C:18]=2[F:41])=[C:15]([F:42])[C:14]([F:43])=[C:13](F)[C:12]=1[F:45].O.Cl>N1C=CC=CC=1>[CH2:1]([O:7][C:13]1[C:12]([F:45])=[C:11]([F:10])[C:16]([C:17]2[C:18]([F:41])=[C:19]([F:40])[C:20]([CH:25]([S:26]([C:29]([F:30])([F:31])[F:32])(=[O:27])=[O:28])[S:33]([C:36]([F:37])([F:38])[F:39])(=[O:35])=[O:34])=[C:21]([F:24])[C:22]=2[F:23])=[C:15]([F:42])[C:14]=1[F:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
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HCID 81031-HexanolHCID 24758Sodium hydrideHCID 21024168(4-(Pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methaneHCID 21885828Hydrate;hydrochloride

생성물 1

HCID 17858624{4-(4-Hexanoxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane수율 94%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
-20 °C

실험 절차

Hexanol (1.5 mL, 12 mmol) was added to a pyridine (10 mL) solution dissolved with 60% sodium hydride containing mineral oil (0.56 g, 14 mmol) at 0° C., and the resultant solution was stirred for 1 hour at room temperature. After the solution was cooled to −20° C., {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane (1.2 g, 2 mmol) was added. The reaction solution was stirred at −20° C. for 5 hours. After the reaction, the solution was acidified with 4 M hydrochloric acid water, and was extracted with diethylether. After drying with magnesium sulfate, the solution was filtrated, and the solvent was removed under reduced pressure. The crude product was purified by sublimation (0.2 to 0.3 torr, 80° C.), and {4-(4-hexanoxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane was obtained at 94% yield (1.27 g, 1.88 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.83 to 0.94 (m, 3H), 1.26 (br, 2H), 1.33 to 1.38 (m, 2H), 1.45 to 1.52 (m, 2H), 1.84 (5, J=6.8 Hz, 2H), 4.38 (t, J=6.8 Hz, 2H), 4.32 (s, 1H); 19F NMR (CDCl3, 282 MHz) δ−75.0 (s, 6F, 2CF3), −128.4 to −128.3 (m, 1F), −133.6 (dt, J=9.1, 21.3 Hz, 1F), −134.8 (dt, J=9.1, 21.3 Hz, 1F), −139.8 to −139.6 (m, 2F), −140.7 (br, 1F), −156.5 (d, J=19.7 Hz, 2F).

후처리

  1. customAfter the reaction
  2. extractionwas extracted with diethylether
  3. dry with materialAfter drying with magnesium sulfate
  4. filtrationthe solution was filtrated
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by sublimation (0.2 to 0.3 torr, 80° C.)

출처 및 근거

ORD 기록
ord-fd6ed328aab84a83b61b8df81f7b1fec
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07339082B2

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