Dimethylformamide → HCID 21919660, Verbindung

HRID 507712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507712
[CH:1]1([C:6]([OH:8])=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.CN(C=O)C.[C:14](Cl)(=[O:18])[C:15](Cl)=O.[CH2:20](N(CC)CC)[CH3:21]>C(Cl)Cl>[CH2:20]([O:8][C:6]1[C:1]2([CH2:2][CH:3]=[CH:4][CH2:5]2)[C:14](=[O:18])[CH:15]=1)[CH3:21]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 8537563-Cyclopentene-1-carboxylic acid

Produkt 1

HCID 21919660HCID 21919660, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of cyclopent-3-ene carboxylic acid (4.0 g, 36.0 mmol) and DMF (0.25 ml) in DCM (30 ml) at 0° was treated dropwise with oxalyl chloride (3.5 ml, 39.0 mmol). After 2 h the reaction mixture was concentrated in vacuo, the residual slurry diluted with Et2O (100 ml) and the resulting precipitate removed by filtration and the filtrate concentrated in vacuo. The resulting oil was diluted with Et2O (50 ml), treated with ethoxyacetylene (40% w/w solution in hexanes, 10 ml) followed dropwise with triethylamine (6 ml, 44.0 mmol) and the reaction stirred for 7 d. Filtration and concentration of the filtrate in vacuo followed by chromatography (SiO2, 5:1 EtOAc:hexanes) gave the title compound as a pale yellow oil (4.3 g, 73%); m/z (ES+, 70V) 164.9 (MH+).

Aufarbeitung

  1. concentrationAfter 2 h the reaction mixture was concentrated in vacuo
  2. additionthe residual slurry diluted with Et2O (100 ml)
  3. customthe resulting precipitate removed by filtration
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe resulting oil was diluted with Et2O (50 ml)
  6. additiontreated with ethoxyacetylene (40% w/w solution in hexanes, 10 ml)
  7. filtrationFiltration and concentration of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3f65cd87a63d46e7b8ab775b435312d0
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786177B2

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