Thionyl Chloride → HCID 53985286, Verbindung

HRID 975820

Reaktionsgleichung

Reaktionsgleichung von HRID 975820
[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH2:18]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][NH:19]1.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)C.CCOC(C)=O>[CH2:18]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][N:19]1[C:5](=[O:7])[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:2][Br:1]

Komponenten

8

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 409979OctahydroisoindoleHCID 167406054-Bromo-2-phenylbutanoic acid

Produkt 1

HCID 53985286HCID 53985286, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Bromo-2-phenylbutanoic acid (4.86 g, 0.02 mol) and thionyl chloride (2.2 mL, 0.03 mol) were refluxed in dichloromethane (100 mL) under nitrogen for 3 hours. The solution was evaporated and flushed with benzene three times. The residue was dissolved in diethyl ether (50 mL) and cooled in an ice bath. Octahydroisoindole (2.5 g, 0.02 mol) and diisopropylethylamine (3.5 mL, 0.02 mol) dissolved in diethyl ether (50 mL) were added and the reaction was stirred for 60 hours at room temperature. TLC (Uniplate/EtOAc) showed essentially complete reaction. The solution was washed with water, sat. NaHCO3, and dried (Na2SO4). Evaporation of solvent left crude product.

Aufarbeitung

  1. customThe solution was evaporated
  2. customflushed with benzene three times
  3. dissolutionThe residue was dissolved in diethyl ether (50 mL)
  4. temperaturecooled in an ice bath
  5. additionwere added
  6. customreaction
  7. washThe solution was washed with water, sat. NaHCO3
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of solvent
  10. waitleft crude product

Quellen und Nachweise

ORD-Eintrag
ord-b5e44369ca664c2f92d3bae4eb1427f9
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610154

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