1,2-Dimethoxyethane → 3-Ethyl-5-phenyl-2,3-dihydrobenzothiepine

HRID 1604494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604494
COCCOC.[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][CH2:22][CH:23]([CH2:26][CH3:27])[CH:24]=O)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Zn].O>[CH2:26]([CH:23]1[CH:24]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21][CH2:22]1)[CH3:27]

Komponenten

5

Edukt 2

HCID 80711,2-DimethoxyethaneHCID 223252232-((2-Benzoylphenylthio)methyl)butyraldehyde

Produkt 1

HCID 223252063-Ethyl-5-phenyl-2,3-dihydrobenzothiepineAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 2.61 g (0.04 mole) of zinc dust and 60 mL of DME was added 7.5 g (0.048 mole) of TiCl3. The reaction mixture was held at reflux for 2 h. A solution of 2.98 g (0.01 mole) of 11 was added dropwise in 1 h. The reaction mixture was held at reflux for 18 h, cooled and poured into water. The organic was extracted into ether. The ether layer was washed with brine and filtered through Celite. The filtrate was dried over MgSO4 and concentrated. The residual oil (2.5 g) was purified by HPLC to give 2.06 g (77%) of 12 as an oil in the second fraction.

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. extractionThe organic was extracted into ether
  5. washThe ether layer was washed with brine
  6. filtrationfiltered through Celite
  7. dry with materialThe filtrate was dried over MgSO4
  8. concentrationconcentrated
  9. customThe residual oil (2.5 g) was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7feb6c149c4242d8b50b9628e9759fd8
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994391

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