Benzenesulfonyl chloride → HCID 18765369、化合物

HRID 480570ノート

反応式

HRID 480570 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.[H-].[Na+].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCOC(C)=O>CN(C=O)C>[C:22]1([S:28]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:17]([O:18][CH3:19])[CH:16]=3)[CH:12]=[CH:13]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2608005-Benzyloxy-6-methoxyindole

生成物 1

HCID 18765369HCID 18765369、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 5-benzyloxy-6-methoxyindole (990 mg, 3.9 mmol) in DMF (3 mL) was added to a solution of NaH (234 mg, 5.9 mmol, 60% in oil) in DMF (1 mL) at 0° C. The ice bath was removed, and the reaction mixture allowed to stir at RT for 30 min. The reaction flask was cooled to 0° C. and PhSO2Cl (0.6 mL, 4.7 mmol) was added via syringe. The ice bath was removed and the reaction mixture stirred at RT for 24 h. Water (25 mL) was added and the aqueous layer extracted with Et2O (4×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give an oil. The residue was purified by column chromatography (25% then 40% EtOAc/hex) to furnish N-phenylsulfonyl 5-benzyloxy-6-methoxyindole as a crystalline solid (1.38 g, 90% yield).

後処理

  1. customThe ice bath was removed
  2. temperatureThe reaction flask was cooled to 0° C.
  3. customThe ice bath was removed
  4. stirringthe reaction mixture stirred at RT for 24 h
  5. additionWater (25 mL) was added
  6. extractionthe aqueous layer extracted with Et2O (4×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give an oil
  12. customThe residue was purified by column chromatography (25%

出典と根拠

ORDレコード
ord-9ee03281ec22404eb947fe151ad67641
出典データセット
uspto-grants-2003_11
特許番号
US06653304B2

反応ノート

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