Diethyl Ether → 1-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

HRID 1684028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684028
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]2[CH2:30][S:29]C(=S)[S:27]2)[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]([SH:27])[CH2:30][SH:29])[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 190418014-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thioneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 190418081-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminum hydride (0.622 g, 16.38 mmole) is added to 60 ml dry diethyl ether. To this slurry is added dropwise 4-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thione (33) (3.40 g, 10.24 mmole) predissolved in 35 ml dry THF. The reaction is stirred under an N2 atmosphere until the solution becomes colorless (4 hours). The reaction is cooled to 0° C. and the excess hydride destroyed with H2O. The reaction mixture is acidified with 10% HCl and immediately extracted with diethyl ether. The organic layer is washed with H2O, dried over MgSO4, filtered and evaporated to a white solid (2.47 g, 84%). NMR: (CDCl3) 2.33,d,1H;2.90,m,1H;3.10,m,1H; 3.59,s,3H;3.85,s,6H;4.03,m,1H;5.10,s,2H;6.53,s,2H Melting Point: 84°-85° C. C,H,S analysis: (theoretical, actual) C (49.63,49.52); H (6.25,6.28); S (22.08,22.16).

Aufarbeitung

  1. custom(4 hours)
  2. customthe excess hydride destroyed with H2O
  3. extractionimmediately extracted with diethyl ether
  4. washThe organic layer is washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a white solid (2.47 g, 84%)

Quellen und Nachweise

ORD-Eintrag
ord-e1fda570ebe5467995354f390c3047b0
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639782

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