Water → 5-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

HRID 1841862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1841862
[I-].[CH2:2]([C:4]1([O:9][C:10](=[O:36])[CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:34][CH3:35])=[C:19]([S+:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[C:23]4[CH:30]=[CH:31][CH:32]=[CH:33][C:22]3=4)[CH:20]=2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3].[F:37][C:38]([F:50])([S:46]([O-:49])(=[O:48])=[O:47])[CH2:39][O:40][C:41](=[O:45])[C:42]([CH3:44])=[CH2:43].C([NH+](CC)CC)C.O>ClCCl>[F:50][C:38]([F:37])([S:46]([O-:49])(=[O:48])=[O:47])[CH2:39][O:40][C:41](=[O:45])[C:42]([CH3:44])=[CH2:43].[CH2:2]([C:4]1([O:9][C:10](=[O:36])[CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:34][CH3:35])=[C:19]([S+:21]3[C:22]4[CH:33]=[CH:32][CH:31]=[CH:30][C:23]=4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=4)[CH:20]=2)=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8]1)[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 867124705-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium iodide

Produkt 1

HCID 867124685-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium iodide (10.0 g, 16.2 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (5.64 g, 17.0 mmol, 1.05 eq) were dissolved in dichloromethane (200 mL) and water (200 mL) and stirred at r.t. overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×250 mL). The combined organic layers were washed with water (3×250 mL), concentrated in vacuo and azeotroped with acetonitrile (2×100 mL) to afford the title compound (10.1 g, 86%) as a white hydroscopic solid. 1H NMR (300 MHz, (d-DMSO) δ: 8.52 (d, J=7.8 Hz, 2H), 8.35 (d, J=7.8 Hz, 2H), 8.27 (dd, J=8.1, 2.1 Hz, 1H), 7.98 (t, J=7.8 Hz, 2H), 7.78 (t, J=7.8 Hz, 2H), 7.55 (d, J=2.1 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 6.09-6.13 (m, 1H), 5.76-5.79 (m, 1H), 4.74 (s, 2H), 4.62 (dd, J=15.6, 15.6 Hz, 2H), 4.05 (s, 3H), 1.83-1.98 (m, 7H), 1.45-1.65 (m, 6H), 0.79 (t, J=6.6 Hz, 3H).

Aufarbeitung

  1. customThe dichloromethane layer was separated
  2. washthe aqueous phase washed with dichloromethane (3×250 mL)
  3. washThe combined organic layers were washed with water (3×250 mL)
  4. concentrationconcentrated in vacuo
  5. customazeotroped with acetonitrile (2×100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-962c0c0181b04624ab65d666f65abb2e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08945814B2

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