Methyl Thioglycolate → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 658168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658168
Cl[C:2]1[C:9]([C:10]#[N:11])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH3:20]S(Cl)(=O)=O>C(OCC)(=O)C>[C:10]([C:9]1[CH:8]=[CH:7][C:6]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:3]=2[CH:2]=1)#[N:11]

Komponenten

6

Edukt 4

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 119617032-Chloro-3-cyanobenzaldehyde

Produkt 1

HCID 11031280Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.5 g (15.1 mmol) of 2-chloro-3-cyanobenzaldehyde are reacted according to the general procedure with 0.90 g (22.7 mmol) of sodium hydride (60% pure) and 1.76 g (16.6 mmol) of methyl mercaptoacetate. The resulting reaction product is initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1) and then dissolved in 30 ml of pyridine, and 650 μl (8.4 mmol) of methanesulfonyl chloride are added. The mixture is stirred at 80° C. for 2 h. After cooling, ethyl acetate is added and the mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, concentrated and dried under high vacuum. This gives 1.63 g (49.9% of theory) of the title compound.

Aufarbeitung

  1. customThe resulting reaction product
  2. customis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
  3. dissolutiondissolved in 30 ml of pyridine
  4. temperatureAfter cooling
  5. washthe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8312e6fda40449a6b48abb2a90b81a60
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076355B2

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