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Hydrochloric Acid → Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 1590716
ノート
印刷プレビュー

反応式

HRID 1590716 の反応式
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=3)[C:9](SC(C)(C)C)=[C:8]2[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1.[CH2:32](S)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([O:27][CH3:32])=[O:26])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 149805763-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

生成物 1

HCID 14980565Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A suspension of 1.0 g of 3-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid (from Example 1 Step B) in 50 mL of CH2Cl2 was treated with 1.3 mL of ethanethiol and 3.47 g of AlCl3 at 0° C. under argon. After 40 min the mixture was poured onto 50 mL 1N HCl, extracted with 3×50 mL of CH2Cl2 washed with 2×50 mL of H2O, dried with MgSO4 and the solvent removed. The residue was dissolved in 10 mL ether and ethereal diazomethane added until all the acid was consumed. The excess solvent was removed and the residue chromatographed on silica gel to afford the title compound.

後処理

  1. extractionextracted with 3×50 mL of CH2Cl2
  2. washwashed with 2×50 mL of H2O
  3. dry with materialdried with MgSO4
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in 10 mL ether
  6. additionethereal diazomethane added until all the acid
  7. customwas consumed
  8. customThe excess solvent was removed
  9. customthe residue chromatographed on silica gel

出典と根拠

ORDレコード
ord-d1a21642c6f040ae86c96b1f4479d9c3
出典データセット
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05204344

反応ノート

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