Dichloromethane → t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

HRID 1668538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668538
ClCCl.[OH:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O>[CH3:32][S:33]([O:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1)(=[O:35])=[O:34]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58105232t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate

Produkt 1

HCID 58105230t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 200 mL round-bottom flask, 50 mL of dichloromethane, 2.78 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate and 2.0 g of diisopropylethylamine were added, and the mixture was stirred at ice temperature for 10 minutes. To the reaction mixture, 0.89 mL of methanesulfonyl chloride was added dropwise, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1) to give 2.28 g of t-butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate as a yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2baea6e96b8544059ce63e17b1a5ff9a
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989446B2

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