Water → (E)-2-(2-(2-(2-tosyloxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine

HRID 1890158ノート

反応式

HRID 1890158 の反応式
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:24][N:23]=1.O>N1C=CC=CC=1>[S:1]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:24][N:23]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 67384227(E)-2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine

生成物 1

HCID 86618273(E)-2-(2-(2-(2-tosyloxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine収率 41%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

Tosyl chloride (52 mg, 0.27 mmol) was added to a solution of compound 9 (43 mg, 0.116 mmol) in pyridine (5.0 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then warmed up to room temperature and stirred for 3 h. Water was added and reaction mixture was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over sodium sulfate and evaporated. The residue was purified by PTLC (4% MeOH in DCM as developing solvent) to give product 10 (25 mg, Yield: 41%): 1H NMR (200 MHz, CDCl3): δ.8.14 (1H, d, J=2.0 Hz), 7.76 (3H, m), 7.39 (2H, d, J=8.8 Hz), 7.32 (2H, d, J=8.0 Hz), 6.87 (2H, m), 6.75 (3H, m), 4.46 (2H, t, J=4.6 Hz), 4.16 (2H, t, J=4.8 Hz), 3.81 (2H, t, J=4.8 Hz), 3.66 (6H, m), 2.99 (6H, s), 2.43 (3H, s), HRMS (EI) m/z calcd. for [C28H34N2O6S]+ 526.2138.

後処理

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 3 h
  3. customreaction mixture
  4. extractionwas extracted with ethyl acetate
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was purified by PTLC (4% MeOH in DCM as developing solvent)

出典と根拠

ORDレコード
ord-54b07da8d9a948148603be31768fe520
出典データセット
uspto-grants-2013_08
特許番号
US08506929B2

反応ノート

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