Perchloric Acid → HCID 66603844, Verbindung

HRID 2406372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2406372
[OH:1][CH:2]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4].Cl(O)(=O)(=O)=O.C(=O)([O-])O.[Na+]>C(OC(C)(C)C)(=O)C>[C:7]([O:1][CH:2]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4])([CH3:8])([CH3:12])[CH3:2]

Komponenten

5

Edukt 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 66603698Methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

Produkt 1

HCID 66603844HCID 66603844, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

A suspension of methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 9, 10.0 g, 23.97 mmol) in tert-butyl acetate (250 mL) was stirred vigorously for 5 minutes prior to the dropwise addition of perchloric acid (70%, 6.15 mL, 71.90 mmol). The resulting mixture was stirred at room temperature for 20 minutes. The mixture was neutralised by addition of a saturated aqueous sodium hydrogen carbonate solution (60 mL) and extracted with ethyl acetate (250 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (250 mL). The combined organic layers were washed with brine (250 mL), dried over MgSO4 and concentrated in vacuo to yield the crude product. The residue was purified by flash column chromatography eluting with ethyl acetate/heptane (10-40%) to give the title compound, 4.26 g, in a 38% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (s, 9H), 1.81-1.92 (m, 4H), 2.66 (s, 3H), 2.79-2.89 (m, 2H), 3.21-3.27 (m, 2H), 3.68 (s, 3H), 5.95 (s, 1H).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 20 minutes
  2. extractionextracted with ethyl acetate (250 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with ethyl acetate (250 mL)
  5. washThe combined organic layers were washed with brine (250 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto yield the crude product
  9. customThe residue was purified by flash column chromatography
  10. washeluting with ethyl acetate/heptane (10-40%)

Quellen und Nachweise

ORD-Eintrag
ord-97ff9ffa227b459e8e6498dc1fa82c35
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809363B2

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