Sodium Iodide → HCID 66759489, Verbindung

HRID 389544

Reaktionsgleichung

Reaktionsgleichung von HRID 389544
[H-].[Na+].C(O[CH:6]([O:10][CH2:11][CH3:12])[C:7]([NH2:9])=[O:8])C.[Br:13][C:14]1[C:18]([CH2:19]Br)=[CH:17][S:16][CH:15]=1.[I-].[Na+].C1[CH2:27][O:26][CH2:25]C1>>[Br:13][C:14]1[C:18]([CH2:19][NH:9][C:7](=[O:8])[CH:6]([O:10][CH2:11][CH3:12])[CH2:25][O:26][CH3:27])=[CH:17][S:16][CH:15]=1

Komponenten

6

Edukt 5

HCID 5238Sodium IodideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 1007652,2-DiethoxyacetamideHCID 133547593-Bromo-4-(bromomethyl)thiophene

Produkt 1

HCID 66759489HCID 66759489, VerbindungAusbeute 35 %

Versuchsvorschrift

To a suspension of sodium hydride (162 mg, 6.74 mmol) in THF (14 mL, 170 mmol) was added 2,2-diethoxyacetamide (949 mg, 6.45 mmol) in portions, followed by 3-bromo-4-(bromomethyl)thiophene (1.50 g, 5.86 mmol) dropwise as a solution in THF (3 mL) and sodium iodide (87.8 mg, 0.586 mmol). The reaction mixture was heated to reflux for 18 h and then concentrated. The residue was then partitioned between water (40 mL) and ethyl acetate (40 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×30 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (5 to 30% ethyl acetate:heptane) afforded 729 mg (35%) of the title compound as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.26-7.29 (m, 1 H), 7.23-7.25 (m, 1 H), 6.99 (br. s., 1 H), 4.83 (s, 1 H), 4.44 (dd, J=6.1, 0.8 Hz, 2 H), 3.21-3.98 (m, 4 H), 1.25 (t, J=6.9 Hz, 6 H); MS (ESI): 322.17, 324.15 [M+H]+; HPLC tR=3.26 min (ZQ3, polar—4 min).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated
  4. customThe residue was then partitioned between water (40 mL) and ethyl acetate (40 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with ethyl acetate (2×30 mL)
  7. dry with materialThe combined organic fractions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by ISCO chromatography (5 to 30% ethyl acetate:heptane)

Quellen und Nachweise

ORD-Eintrag
ord-7273c1aef4604380aa8663eaf10690f6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378104B2

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