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

HRID 2173969노트

반응식

HRID 2173969 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-329d3019688f4eadacb036c8cc4fe3ee
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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