Dimethylformamide → 4-(Triethoxysilyl)benzophenone

HRID 571451

Reaktionsgleichung

Reaktionsgleichung von HRID 571451
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]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13830TriethoxysilaneHCID 5696384-Iodobenzophenone

Produkt 1

HCID 585606374-(Triethoxysilyl)benzophenoneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

[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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7bf9c08250e4960be2613b1bab1f0da
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024093B2

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