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Water → 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

HRID 1841860
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HRID 1841860 반응식
[Br-].[CH2:2]([C:4]1([O:9][C:10](=[O:34])[CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([S+:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22]4[CH:29]=[CH:30][CH:31]=[CH:32][C:21]3=4)=[CH:15][C:14]=2[CH3:33])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3].[F:35][C:36]([F:48])([S:44]([O-:47])(=[O:46])=[O:45])[CH2:37][O:38][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41].C([NH+](CC)CC)C.O>ClCCl>[F:48][C:36]([F:35])([S:44]([O-:47])(=[O:46])=[O:45])[CH2:37][O:38][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41].[CH2:2]([C:4]1([O:9][C:10](=[O:34])[CH2:11][O:12][C:13]2[C:14]([CH3:33])=[CH:15][C:16]([S+:20]3[C:21]4[CH:32]=[CH:31][CH:30]=[CH:29][C:22]=4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]3=4)=[CH:17][C:18]=2[CH3:19])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3]
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참가 물질

5

반응물 3

HCID 962WaterHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 867124585-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide

생성물 1

HCID 867124655-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate수율 93.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide (20.0 g, 37.1 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (1.1 eq, 40.8 mmol, 13.5 g) were dissolved in dichloromethane (250 mL) and water (250 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 (4×250 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×250 mL) to afford the title compound (23.8 g, 93%) as a white solid. 1H NMR (300 MHz, (CD3)2CO) δ: 8.53 (d, J=7.8 Hz, 2H), 8.36 (d, J=7.8 Hz, 2H), 8.04 (t, J=7.5 Hz, 2H), 7.83 (t, J=7.8 Hz, 2H), 7.51 (visual s, 2H), 6.14-6.16 (m, 2H), 5.66-5.69 (m, 2H), 4.75 (dd, J=15.6, 15.6 Hz, 2H), 4.57 (s, 2H), 2.30 (s, 6H), 2.03-2.11 (m, 2H), 2.02 (q, J−7.8 Hz, 2H), 1.93-1.95 (m, 3H), 1.55-1.6 (m, 6H), 0.84 (t, J=7.5 Hz, 3H).

후처리

  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 (4×250 mL)
  4. concentrationconcentrated in vacuo and residual water
  5. customremoved via azeotrope with acetonitrile (2×250 mL)

출처 및 근거

ORD 기록
ord-ae65688f5ac64c05bbffc708bbf412fa
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08945814B2

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