Sodium Sulfide → Methyl 4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate

HRID 2090126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090126
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12]Cl)=[C:8]([CH2:10]Cl)[CH:9]=1)=[O:4].[S-2:14].[Na+].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[CH2:12][S:14][CH2:10][C:8]=2[CH:9]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 14804Sodium SulfideHCID 11096691Methyl 4,5-bis(chloromethyl)thiophene-2-carboxylate

Produkt 1

HCID 3441857Methyl 4,6-dihydrothieno[3,4-b]thiophene-2-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 4.8 g (20 mmol) (2) in 240 mL methanol was heated up and kept mild boiling. Sodium sulfide solution (1.7 g, 22 mmol) in 160 mL methanol was added dropwise in 2 h. After cooling of the reaction mixture, the precipitate was filtered off. The solvent was removed by evaporation and the residue was washed by water. Column chromatography on silica gel using dichloromethane yielded the pure title compound as a white solid 2.0 g (50%). 1HNMR (CDCl3): δ 3.87 (3H, s), 4.05-4.06 (2H, t, J=3 Hz), 4.19-4.20 (2H, t, J=3 Hz), 7.48 (1H, s). 13CNMR (CDCl3): δ 33.12, 33.47, 52.19, 127.90, 137.30, 143.90, 146.64, 162.51.

Aufarbeitung

  1. temperatureAfter cooling of the reaction mixture
  2. filtrationthe precipitate was filtered off
  3. customThe solvent was removed by evaporation
  4. washthe residue was washed by water

Quellen und Nachweise

ORD-Eintrag
ord-4b9d280b64f7479881d6a7f054971f39
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436134B2

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