2-Methyl-3-furanthiol → 4-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

HRID 723072

Reaktionsgleichung

Reaktionsgleichung von HRID 723072
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8](Br)[CH:9]=1)=[O:4].[CH3:14][C:15]1[O:16][CH:17]=[CH:18][C:19]=1[SH:20]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([S:20][C:19]2[CH:18]=[CH:17][O:16][C:15]=2[CH3:14])[CH:9]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 342862-Methyl-3-furanthiolHCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylate

Produkt 1

HCID 695867094-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 532 mg, 2 mmol), 2-methyl-furan-3-thiol (600 mg, 5.26 mmol), and DMAP-polystyrene resin (2 g, 2.86 mmol) were stirred in THF (10 mL) for 12 h at rt. The resin was filtered and washed with several portions of DCM (100 mL total volume). The filtrate was concentrated in vacuo and the yellow residue (480 mg, 80%) was used without further purification. 1H-NMR (CDCl3): δ 7.46 (d, 1H, J=1.9 Hz), 7.05 (s, 1H), 6.43 (d, 1H, J=1.9 Hz), 3.90 (s, 3H), 2.38 (s, 3H).

Aufarbeitung

  1. filtrationThe resin was filtered
  2. washwashed with several portions of DCM (100 mL total volume)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe yellow residue (480 mg, 80%) was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d22bd471740c4942b41b1c5b6c0f7975
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138530B2

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