Water → 4a'-methyl-(4'H,5'H,7'H)-spiro[1,3-dithiolane-2,2'-naphthalen]-5'(6'H)-one

HRID 1723914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723914
[CH3:1][C:2]12[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]1=[CH:7][C:5](=O)[CH2:4][CH2:3]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:25]([SH:28])[CH2:26][SH:27].O>C(O)(=O)C>[CH3:1][C:2]12[C:12](=[O:13])[CH2:11][CH2:10][CH:9]=[C:8]1[CH2:7][C:5]1([S:28][CH2:25][CH2:26][S:27]1)[CH2:4][CH2:3]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 109021,2-EthanedithiolHCID 89262(+-)-Wieland-Miescher ketone

Produkt 1

HCID 873063524a'-methyl-(4'H,5'H,7'H)-spiro[1,3-dithiolane-2,2'-naphthalen]-5'(6'H)-oneAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of Wieland-Miescher ketone (5.87 g, 33.0 mmol) in glacial acetic acid (40 mL) was added p-toluenesulfonic acid (2.94 g) followed by dropwise addition of 1,2-ethanedithiol over a 1 hour period. The reaction mixture was stirred at room temperature for another 4 hours, poured into 30 mL water, and stirred for 15 minutes. The white solid was filtered off, washed successively with water, diluted with NaHCO3 solution and water, and then dried to yield thioketal 239 (7.33 g, 87.3%) as a white solid. 1H NMR (CDCl3) δ 1.50-2.70 (m, 10H), 3.20-3.40 (m, 4H), 5.67 (s, 1H); 13C NMR (CDCl3) 212.92, 141.23, 128.04, 64.81, 49.43, 40.11, 39.62, 37.92, 37.57, 30.81, 30.69, 24.73, 24.57.

Aufarbeitung

  1. stirringstirred for 15 minutes
  2. filtrationThe white solid was filtered off
  3. washwashed successively with water
  4. additiondiluted with NaHCO3 solution and water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-13f48d8542d34dd391c155f3c1bbe33c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485660B2

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