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2-((2-Benzoylphenylthio)methyl)-2-ethylhexanal → 3-Butyl-3-ethyl-5-phenyl-2,3-dihydrobenzothiepine

HRID 2229503
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2229503
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][CH2:16][C:17]([CH2:24][CH3:25])([CH2:20][CH2:21][CH2:22][CH3:23])[CH:18]=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>COCCOC.[Cl-].[Na+].O.[Zn]>[CH2:20]([C:17]1([CH2:24][CH3:25])[CH:18]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][CH2:16]1)[CH2:21][CH2:22][CH3:23]
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Komponenten

5

Edukt 1

HCID 116028262-((2-Benzoylphenylthio)methyl)-2-ethylhexanal

Produkt 1

HCID 223252133-Butyl-3-ethyl-5-phenyl-2,3-dihydrobenzothiepineAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of 2.6 g (0.04 mole) of zinc dust, 7.2 g (0.047 mole) of TiCl, and 80 mL of anhydrous ethylene glycol dimethyl ether (DME) was held at reflux for 2 h. The reaction mixture was cooled to 5° C. To the reaction mixture was added dropwise a solution of 3.54 g (0.01 mole) of 2 in 30 mL of DME in 40 min. The reaction mixture was stirred at room temperature for 16 h and then was held at reflux for 2 h and cooled before being poured into brine. The organic was extract into methylene chloride. The methylene chloride extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by HPLC (hexane) to give 1.7 g (43%) of 3 as an oil in the first fraction. The second fraction was discarded and the third fraction was further purified by HPLC (hexane) to give 0.07 g (2%) of 4a in the earlier fraction and 0.1 g (3%) of 4b in the later fraction.

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. extractionThe organic was extract into methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8a4513de67044b1ab16bb81c530491ce
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06420417B1

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