Ethylene Glycol → 5,5-(Ethylenedioxy)-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphtalen-2-one

HRID 1723909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723909
[CH3:1][C:2]12[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[CH3:14][C:15]1(CC)OCC[O:16]1.C(O)CO>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:14]1[CH2:15][O:16][C:12]2([CH2:11][CH2:10][CH2:9][C:8]3[C:2]2([CH3:1])[CH2:3][CH2:4][C:5](=[O:6])[CH:7]=3)[O:13]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 610672-Ethyl-2-methyl-1,3-dioxolaneHCID 89262(+-)-Wieland-Miescher ketone

Produkt 1

HCID 109221015,5-(Ethylenedioxy)-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphtalen-2-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 521998p-Toluenesulfonic acid monohydrateKatalysator

Versuchsvorschrift

A mixture of Wieland-Miescher ketone (5.086 g, 28.44 mmol), 2-methyl-2-ethyl-1,3-dioxolane (19.38 mL, 155.0 mmol), ethylene glycol (0.358 mL, 6.43 mmol) and p-toluenesulfonic acid monohydrate (0.4 g, 2.13 mmol) was stirred at room temperature for 30 hours. The reaction was quenched with dropwise addition of triethylamine, diluted with 20 mL of benzene, washed with water, dried over MgSO4, and concentrated under vacuum. The product was triturated from hexanes to yield monoacetal 201 (5.92 g, 94%). 1H NMR (CDCl3) δ 1.36 (s, 3H), 1.6-2.0 (m, 5H), 2.2-2.5 (m, 5H), 3.9-4.1 (m, 4H), 5.80 (d, J=Hz, 1H); 13C NMR (CDCl3) 198.91, 167.55, 125.38, 125.37, 112.12, 65.16, 64.84, 44.81, 33.70, 31.22, 29.81, 26.62, 21.51, 20.27.

Aufarbeitung

  1. customThe reaction was quenched with dropwise addition of triethylamine
  2. additiondiluted with 20 mL of benzene
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe product was triturated from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8c0c3149fee94f4e8603612118f22d6e
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485660B2

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