Dimethylformamide → (S)-5-Oxotetrahydrofuran-2-carbonyl chloride

HRID 60737

Reaktionsgleichung

Reaktionsgleichung von HRID 60737
[O:1]=[C:2]1[O:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.CN(C=O)C.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl>[O:1]=[C:2]1[O:6][C@H:5]([C:7]([Cl:18])=[O:9])[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 636468(2S)-5-oxooxolane-2-carboxylic acid2×

Produkt 1

HCID 10975648(S)-5-Oxotetrahydrofuran-2-carbonyl chlorideAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2S)-5-oxotetrahydrofuran-2-carboxylic acid (compound 28a, 70 g, 539 mmol) and a drop of DMF in anhydrous DCM (500 mL) was added oxalyl dichloride (137 g, 1.07 mol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. The reaction was then concentrated in vacuo to afford 70 g crude product of (2S)-5-oxotetrahydrofuran-2-carbonyl chloride (compound 28b), which was used in next step without further purification.

Aufarbeitung

  1. concentrationThe reaction was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77eed8f0a2d446d19676e36e967d82c0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441008B2

Verknüpfte Notizen

Wird geladen…