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

HRID 1841862ノート

反応式

HRID 1841862 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 867124685-(5-((2-(1-ethylcyclopentyloxy)-2-oxoethoxy)carbonyl)-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate収率 86.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-962c0c0181b04624ab65d666f65abb2e
出典データセット
uspto-grants-2015_02
特許番号
US08945814B2

反応ノート

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