Dimethylformamide → 4-(Triethoxysilyl)benzophenone

HRID 571451

反応式

HRID 571451 の反応式
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]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13830TriethoxysilaneHCID 5696384-Iodobenzophenone

生成物 1

HCID 585606374-(Triethoxysilyl)benzophenone収率 80%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-d7bf9c08250e4960be2613b1bab1f0da
出典データセット
uspto-grants-2015_05
特許番号
US09024093B2

関連ノート

読み込み中…