2-Bromopyridine → HCID 21187637, Verbindung

HRID 1383766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383766
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[O:15][CH2:14]1.C(=O)(O)[O-:25].[Na+]>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1([OH:25])[CH2:20][CH2:21][C:16]2([O:23][CH2:13][CH2:14][O:15]2)[CH2:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 79732-BromopyridineHCID 516892Sodium BicarbonateHCID 123480741,4-Dioxaspiro[4.5]decan-6-oneHCID 178418339Butyllithium

Produkt 1

HCID 21187637HCID 21187637, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-bromo-pyridine (10 g, 63.3 mmol) in tetrahydrofuran (200 mL) at −78° C. under an argon atmosphere was added a solution of n-butyllithium (26 mL of 2.5N solution, 65 mmol). The solution was stirred at −78° C. for 10 minutes and then a solution of cyclohexanedione monoethylene ketal (10 g, 64 mmol) in tetrahydrofuran(50 mL) was added. The reaction was allowed to warm to room temperature and poured into a saturated solution of sodium bicarbonate (mL) the mixture was extracted with ethyl acetate. The combined ethyl acetate fractions were dried over anhydrous sodium sulfate, filtered, and concentrated at reduced pressure. The residue was chromatographed over silica gel eluting with 25% to 50% ethyl acetate/hexane to give the product.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate fractions were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed over silica gel eluting with 25% to 50% ethyl acetate/hexane
  7. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-71685d845e684a98b068436b77e94b05
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255315B1

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