2-Bromoethyl methyl ether → Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

HRID 336603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336603
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]([O:13][CH3:14])=[O:12])[CH2:8]2.C([N-]C(C)C)(C)C.[Li+].[CH3:23][O:24][CH2:25][CH2:26]Br>O1CCCC1>[CH3:23][O:24][CH2:25][CH2:26][C:2]1([C:11]([O:13][CH3:14])=[O:12])[CH:1]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]1[CH2:4]3)[CH2:8]2

Komponenten

5

Edukt 3

HCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamideHCID 12600018Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate

Produkt 1

HCID 89498778Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of EXAMPLE 56A (0.314 g) in tetrahydrofuran (5 mL) was added dropwise lithium diisopropylamide (1.401 mL) at −78° C. The reaction mixture was stirred for 60 minutes and 2-bromoethyl methyl ether (0.562 g) was added. The reaction mixture was slowly warmed up to room temperature, stirred at room temperature overnight, quenched with saturated aqueous NH4Cl solution (2 mL), and extracted with ether. The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes).

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. customquenched with saturated aqueous NH4Cl solution (2 mL)
  3. extractionextracted with ether
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-974c7881d77149fd9fb57a810cf7c4c9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889675B2

Notizen zur Reaktion

Wird geladen…