Magnesium perchlorate → Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate

HRID 1394035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394035
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12]O.[CH3:14][O:15][C:16]([O:20][Si](C)(C)C)=[C:17](C)C.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>ClCCl.O>[CH3:14][O:15][C:16](=[O:20])[CH2:17][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 24840Magnesium perchlorateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 4255293(5-methoxy-1H-indol-3-yl)methanol

Produkt 1

HCID 54357260Methyl 3-(5-methoxy-1H-indol-3-yl)propanoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-methoxy-1H-indol-3yl-methanol 141 (115 mg, 0.643 mmol) dissolved in dichloromethane (3 ml), (1-methoxy-2-methyl-propenyloxy)-trimethylsilane (200 mg, 1 mmol) and magnesium perchlorate (164 mg, 0.74 mmol) were added. The reaction was allowed to stir at ambient temperature for 3-4 hours after after which the mixture was diluted with water (50 ml) and dichloromethane (DCM, 100 mL). The organic layer was separated and washed with water (50 mL; 3×). The organic layer was washed once with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give an oil and purified with flash chromatography (silica with 80% hexane, 20% ethyl acetate to afford 142 as a light colored oil (150 mg; 88% yield; M+1=262.3).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water (50 mL; 3×)
  3. washThe organic layer was washed once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. custompurified with flash chromatography (silica with 80% hexane, 20% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8bf7ff7d2cbd46949d9586d586bd732a
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348338B2

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