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

HRID 2307477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307477
[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 MgSO4and 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. customdried over MgSO4and
  5. concentrationconcentrated under vacuum
  6. customThe product was triturated from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7dd101d150b24ff193404c7288ffdf86
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831093B2

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