Water → 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate

HRID 1841865노트

반응식

HRID 1841865 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].[OH:37][C:38]12[CH2:47][CH:42]3[CH2:43][CH:44]([CH2:46][CH:40]([CH2:41]3)[CH2:39]1)[CH2:45]2.[Na].[C:49]([O:52][CH:53]([CH3:64])[C:54]([F:63])([F:62])[C:55]([F:61])([F:60])[S:56]([O-:59])(=[O:58])=[O:57])(=[O:51])[CH3:50].O>ClCCl>[OH:37][C:38]12[CH2:39][CH:40]3[CH2:46][CH:44]([CH2:43][C:42]([CH2:50][C:49]([O:52][CH:53]([CH3:64])[C:54]([F:63])([F:62])[C:55]([F:61])([F:60])[S:56]([O-:59])(=[O:58])=[O:57])=[O:51])([CH2:41]3)[CH2:47]1)[CH2:45]2.[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 867124715-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromideHCID 1317324103-Hydroxyadamantane acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate sodium

생성물 1

HCID 867124745-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate수율 86%

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 (1.8 g, 3.21 mmol) and sodium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate (1.44 g, 3.37 mmol) were dissolved in dichloromethane (100 mL) and water (100 mL) and stirred at r.t. overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×100 mL). The combined organic layers were washed with water (6×200 mL) and concentrated in vacuo to afford the title compound (2.44 g, 86%) as a white solid. 1H NMR (500 MHz, ((CD3)2SO) δ: 8.53 (d, J=8 Hz, 2H), 8.35 (d, J=8 Hz, 2H), 8.03 (t, J=7 Hz, 2H), 7.83 (d, J=8 Hz, 2H), 7.51 (s, 2H), 7.40 (d, J=8 Hz, 2H), 7.31 (dt, J=8, 0.5 Hz, 2H), 7.24 (dt, J=7.5, 1 Hz, 1H), 4.65 (s, 2H), 4.31 (t, J=6.5 Hz, 2H), 2.80-2.82 (m, 2H), 2.65 (tt, J=14, 6.5 Hz, 2H), 2.29 (s, 6H), 1.72-1.81 (m, 10H), 1.65-1.67 (m, 4H), 1.56-1.59 (m, 2H).

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 (6×200 mL)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-003f90513561479aaa1c61ca4b2c27d5
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08945814B2

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