Benzenesulfonyl chloride → HCID 18765369、化合物

HRID 1159862ノート

反応式

HRID 1159862 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 7369Benzenesulfonyl chlorideHCID 2608005-Benzyloxy-6-methoxyindole

生成物 1

HCID 18765369HCID 18765369、化合物収率 84%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 14798Sodium Hydroxide溶媒

実験手順

To 5-benzyloxy-6-methoxyindole (5.0 g, 20 mmol), benzenesulfonyl chloride (5.2 g, 30 mmol) and tetrabutylammonium hydrogen sulfate (2.0 g, 6 mmol) DCM (200 mL) and 4M NaOH (50 mL) were added. The reaction mixture was allowed to stir at room temperature over night. The organic layer was collected and the aqueous phase was washed with DCM (2×30 mL). The combined organic layers were then washed with brine (2×50 mL). Drying, (MgSO4), filtration and evaporation afforded a brown oil. The product precipitated when adding diethyl ether. Recrystallization from MeOH afforded the title compound in 84% yield (6.55 g) as light yellow crystals. MS (ESI+) for C22H19NO4S m/z 394 (M+H)+.

後処理

  1. customThe organic layer was collected
  2. washthe aqueous phase was washed with DCM (2×30 mL)
  3. washThe combined organic layers were then washed with brine (2×50 mL)
  4. customDrying
  5. filtration, (MgSO4), filtration and evaporation
  6. customafforded a brown oil
  7. customThe product precipitated when
  8. additionadding diethyl ether
  9. customRecrystallization from MeOH

出典と根拠

ORDレコード
ord-50a92435fe054cdebc3c57b3be45f1a9
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

反応ノート

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