Dimethylformamide → 4-(Triethoxysilyl)benzophenone

HRID 571451

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HRID 571451 반응식
I[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.CN(C=O)C.C(N(CC)CC)C.[CH2:28]([O:30][SiH:31]([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])[CH3:29]>CCOCC>[CH2:28]([O:30][Si:31]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH3:29]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13830TriethoxysilaneHCID 5696384-Iodobenzophenone

생성물 1

HCID 585606374-(Triethoxysilyl)benzophenone수율 80%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
80 °C

실험 절차

[Rh(cod)(MeCN)2]BF4 (11.0 mg, 0.0300 mmol, 0.0300 equiv) and 4-iodobenzophenone (307 mg, 1.00 mmol, 1.00 equiv) were charged in 10 mL vial capped with a rubber septum. The vial was evacuated and backfilled with nitrogen. To this vial, DMF (4 mL), triethylamine (0.420 mL, 3.00 mmol, 3.00 equiv) and triethoxysilane (0.360 mL, 2.00 mmol, 2.00 equiv) were added. The reaction mixture was stirred at 80° C. for 2 h, then cooled to 23° C. The mixture was diluted with ether (50 mL) and washed three times with water (3×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Kugelrohr distillation to give 275 mg of the title compound as a colorless oil (80% yield). Rf=0.45 (hexanes/EtOAc 3:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23° C., δ): 7.82−7.77 (m, 6H), 7.59 (t, J=7.5 Hz, 1H), 7.48 (dd, J=7.5 Hz, 7.5 Hz, 2H), 3.90 (q, J=7.0 Hz, 6H), 1.27 (t, J=7.0 Hz, 9H). 13C NMR (125 MHz, CDCl3, 23° C., δ): 196.84, 139.05, 137.29, 136.34, 134.66, 132.54, 130.11, 129.00, 128.28, 58.91, 18.21. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M+Na]+, 367.13361. Found, 367.13347.

후처리

  1. customvial capped with a rubber septum
  2. customThe vial was evacuated
  3. temperaturecooled to 23° C
  4. washwashed three times with water (3×20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was purified by Kugelrohr distillation

출처 및 근거

ORD 기록
ord-d7bf9c08250e4960be2613b1bab1f0da
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024093B2

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