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Pyridine → Tris-(4-butoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

HRID 277681
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HRID 277681 반응식
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C(C)(C)C)=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)(C)(C)[CH3:2].N1[CH:30]=[CH:29][CH:28]=[CH:27]C=1.[F:31][C:32]([F:47])([F:46])[CH:33]([F:45])[C:34]([F:44])([F:43])[S:35]([O:38][Si](C)(C)C)(=[O:37])=[O:36].[Mg].[C:49]([O:53][C:54]1[CH:59]=[CH:58][C:57](Cl)=[CH:56][CH:55]=1)([CH3:52])(C)C.O1CC[CH2:63][CH2:62]1>O>[F:47][C:32]([F:31])([F:46])[CH:33]([F:45])[C:34]([F:43])([F:44])[S:35]([O-:38])(=[O:36])=[O:37].[CH2:49]([O:53][C:54]1[CH:55]=[CH:56][C:57]([S+:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:33][CH3:34])=[CH:7][CH:8]=2)[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:30][CH2:29][CH2:28][CH3:27])=[CH:18][CH:19]=2)=[CH:58][CH:59]=1)[CH2:52][CH2:62][CH3:63]
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참가 물질

8

반응물 6

HCID 1049PyridineHCID 8028Tetrahydrofuran2회HCID 1404581-Chloro-4-tert-butoxybenzeneHCID 5462224MagnesiumHCID 15389810Bis(4-tert-butoxyphenyl) sulfoxideHCID 22625546Trimethylsilyl 3,3,3,2,1,1-hexafluoropropane sulfonate

생성물 1

HCID 86757888
Tris-(4-butoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
5 °C

실험 절차

To a stirred solution of 60.0 g (0.164 mol) of bis-(4-t-butoxyphenyl) sulfoxide in 26.8 g (0.34 mol) of pyridine and 400 ml of tetrahydrofuran was dropped 75.6 g (0.34 mol) of trimethylsilyl 3,3,3,2,1,1-hexafluoropropane sulfonate while keeping the temperature below −5° C. with a salted ice bath. After completion of the addition, the reaction temperature was raised to 5° C., followed by stirring for 20 minutes. A Grignard solution was prepared from 8.4 g (0.34 mol) of magnesium, 100 g of tetrahydrofuran and 68.6 g (0.38 mol) of 4-t-butoxy chlorobenzene, and added dropwise to the above solution at 0° C. The mixture was stirred for 2 hours at this temperature. Then water was added to decompose the excess Grignard reagent, and the inorganic salts were removed by filtration. The solution was concentrated to about 160 ml and extracted with a mixture of 1200 ml of dichloromethane, 600 g of a saturated aqueous solution of ammonium chloride and 600 ml water. The organic phase was washed twice with water and dried. The solvent was removed to yield an oily product which was then purified by column chromatography on silica gel using dichloromethane as the eluant. Thus, tris-(4-butoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate was obtained as a slightly yellowish powder (m.p. 107° C.). The structure was confirmed by 1H-NMR (CDCl3) with δ=1.42 (s, 27H), 5.14-5.52 (d[m], 1H), 7.17-7.20 (d, 6H) and 7.55-7.60 ppm (d, 6H).

후처리

  1. customthe temperature below −5° C.
  2. additionAfter completion of the addition
  3. additionadded dropwise to the above solution at 0° C
  4. stirringThe mixture was stirred for 2 hours at this temperature
  5. customthe inorganic salts were removed by filtration
  6. concentrationThe solution was concentrated to about 160 ml
  7. extractionextracted with a mixture of 1200 ml of dichloromethane, 600 g of a saturated aqueous solution of ammonium chloride and 600 ml water
  8. washThe organic phase was washed twice with water
  9. customdried
  10. customThe solvent was removed
  11. customto yield an oily product which
  12. customwas then purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-a5976dba59f542d09a45f1c17e51a684
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06358665B1

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