1,2-Ethanedithiol → HCID 86615015, Verbindung

HRID 1436695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436695
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:16]=[C:15]([C:17]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)=O)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[CH2:25]([SH:28])[CH2:26][SH:27].B(F)(F)F.CCCCOCCCC>ClCCl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:16]=[C:15]([C:17]2([C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)[S:28][CH2:25][CH2:26][S:27]2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Komponenten

5

Edukt 3

HCID 109021,2-EthanedithiolHCID 68970Boron, trifluoro(1,1'-oxybis(butane))-, (T-4)-HCID 68816228HCID 68816228, Verbindung

Produkt 1

HCID 86615015HCID 86615015, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 5-(furan-2-carbonyl)-N-methyl-N-propyl-isophthalamic acid methyl ester (290 mg, 0.88 mmol) in dichloromethane (2 mL). Cool to 0° C., add a solution of ethane-1,2-dithiol (0.22 mL, 2.2 mmol) and then add a solution of boron trifluoride dibutyl etherate (0.66 mL, 5.2 mmol) in dichloromethane (5 mL). Warm the mixture to room temperature and stir overnight. Quench with water and dilute with dichloromethane. Wash the organic layer by saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes) to give the title compound (38%).

Aufarbeitung

  1. temperatureWarm the mixture to room temperature
  2. customQuench with water
  3. additiondilute with dichloromethane
  4. washWash the organic layer by saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-27162fc6cd8740fca96c25c8d4bfccff
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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