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

HRID 478883
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 478883
[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 TiCl3 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 vacu. 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. temperaturecooled
  3. extractionThe organic was extract into methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacu
  7. customThe residue was purified by HPLC (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7dfb1bf874594a5dae7270c0356bd53f
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06642268B2

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