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Water → 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

HRID 1841867
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HRID 1841867 반응식
[Br-].[CH3:2][C:3]1[CH:4]=[C:5]([S+:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]2=3)[CH:6]=[C:7]([CH3:23])[C:8]=1[O:9][CH2:10][C:11](=[O:22])[O:12][C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14].[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].[CH3:23][C:7]1[CH:6]=[C:5]([S+:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]2=3)[CH:4]=[C:3]([CH3:2])[C:8]=1[O:9][CH2:10][C:11](=[O:22])[O:12][C:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:15])[CH3:14]
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참가 물질

5

반응물 3

HCID 962WaterHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 867124715-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide

생성물 1

HCID 867124765-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide (7.00 g, 12.5 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (4.21 g, 12.7 mmol) were dissolved in dichloromethane (100 mL) and water (100 mL) and stirred at room temperature overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×100 mL). The combined organic layers were washed with water (4×100 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×100 mL) to afford the title compound (7.07 g, 80%) as a white solid. 1H NMR (300 MHz, (CD3)2CO) δ: 8.53 (d, J=7.8 Hz, 2H), 8.37 (d, J=7.8 Hz, 2H), 8.03 (t, J=7.8 Hz, 2H), 7.82 (t, J=7.8 Hz, 2H), 7.52 (s, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.32 (t, J=8.1 Hz, 2H), 7.26 (t, J=8.1 Hz, 1H), 6.12-6.19 (m, 1H), 5.68-5.71 (m, 1H), 4.76 (t, J=15.6 Hz, 2H), 4.66 (s, 2H), 2.28 (s, 6H), 1.94 (s, 3H), 1.77 (s, 6H).

후처리

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

출처 및 근거

ORD 기록
ord-1a970b6ea723480ebd3df51f4ce331ad
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08945814B2

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