p-Toluenesulfonic acid monohydrate → (5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

HRID 2173969ノート

反応式

HRID 2173969 の反応式
[Cl:1][C:2]1[C:3]([CH2:22][O:23]C2CCCCO2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.CC1C=CC(S(O)(=O)=O)=CC=1.O>CCO>[Cl:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867015385-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole

生成物 1

HCID 86701537(5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of (±)-5-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole (4.1 g, 9.5 mmol) and TsOH.H2O (359 mg, 1.9 mmol) in EtOH (50 mL) was stirred at room temperature for 21 h. The reaction mixture was concentrated. The mixture was diluted with CH2Cl2. The organic phase was successively washed with 5% aq. NaHCO3, H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, without need of further purification. 1H NMR (400 MHz, ACETONITRILE-d3) δ 7.84 (d, J=3.79 Hz, 1H), 7.59 (d, J=8.34 Hz, 2H), 7.33 (d, J=8.34 Hz, 2H), 7.10 (s, 1H), 7.00 (d, J=3.79 Hz, 1H), 4.84 (d, J=5.81 Hz, 2H), 3.14 (t, J=5.81 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionThe mixture was diluted with CH2Cl2
  3. washThe organic phase was successively washed with 5% aq. NaHCO3, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-329d3019688f4eadacb036c8cc4fe3ee
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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