Acetic Anhydride → (4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanol

HRID 1645522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645522
[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N+:19]([O-])=[C:18]([CH3:23])[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][O:4]1)[CH3:2].C(N(CC)CC)C.C(OC(=O)C)(=[O:34])C>>[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH2:23][OH:34])[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][O:4]1)[CH3:2]

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 597925064-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-2,3-dimethylpyridine 1-oxide

Produkt 1

HCID 59792375(4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanolAusbeute 59,6 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The 4-(2-(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-2,3-dimethylpyridine 1-oxide (947 mg, 2.79 mmol) obtained in the step (4f) was mixed with acetic anhydride (10 ml). To the mixture, triethylamine (0.6 ml, 4.3 mmol) was added and stirred at 50° C. for 2 hours. The reaction mixture was concentrated and methanol (10 ml) was added to the residue and thereafter, a 5N aqueous sodium hydroxide solution (7 ml) was added and stirred at room temperature for one hour. To the mixture, a saturated aqueous ammonium chloride solution (7 ml) was added and the pH of the resultant solution was adjusted to about 10. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 2N aqueous sodium hydroxide solution, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-4/1 gradient) and a desired fraction(s) was concentrated to obtain the title compound (564 mg, yield: 59.6%) as a light yellow solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionmethanol (10 ml) was added to the residue
  3. additiona 5N aqueous sodium hydroxide solution (7 ml) was added
  4. stirringstirred at room temperature for one hour
  5. additionTo the mixture, a saturated aqueous ammonium chloride solution (7 ml) was added
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washthe organic layer was washed with a 2N aqueous sodium hydroxide solution, water
  8. dry with materiala saline solution, dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-4/1 gradient)
  12. concentrationa desired fraction(s) was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb0e93aec87340ecbf3363501c1c8c9e
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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