Indole → HCID 68004074, Verbindung

HRID 1621269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621269
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([O:14][CH3:15])(=[O:13])[CH2:11][SH:12].II.[I-].[K+]>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:12][CH2:11][C:10]([O:14][CH3:15])=[O:13])=[CH:2]1

Komponenten

7

Edukt 4

HCID 798IndoleHCID 807IodineHCID 4875Potassium IodideHCID 16907Methyl Thioglycolate

Produkt 1

HCID 68004074HCID 68004074, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of indole (3.00 g, 25.6 mmol) and methyl thioglycolate (2.40 mL, 25.6 mmol) in methanol:water (80 mL:20 mL) was added iodine (6.50 g, 25.6 mmol) and potassium iodide (4.25 g, 25.6 mmol). The reaction mixture was stirred at ambient temperature for 60 hours. Methanol was removed in vacuo and the aqueous layer diluted with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated in vacuo and the resulting residue was purified on a silica gel column (0-100% ethyl acetate:hexanes over 33 min) to afford the desired product. LCMS>99% at 254 nm, RT=1.29 min, m/z=222 (M+1).

Aufarbeitung

  1. customMethanol was removed in vacuo
  2. additionthe aqueous layer diluted with a saturated solution of sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customthe resulting residue was purified on a silica gel column (0-100% ethyl acetate:hexanes over 33 min)

Quellen und Nachweise

ORD-Eintrag
ord-d09a43425dc143e8a1096a27ea59f413
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772509B2

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