Dimethyl Sulfoxide → (2-Ethoxycarbonyl)-(1-formyl)ethylene oxide

HRID 1681286

Reaktionsgleichung

Reaktionsgleichung von HRID 1681286
[CH3:1][CH2:2][O:3][C:4]([C:6]1([CH2:9][OH:10])[O:8][CH2:7]1)=[O:5].CS(C)=O.[C:15](Cl)(=[O:19])[C:16](Cl)=O.[CH2:21](N(CC)CC)C.CCCCC.[C:33]([O:36][CH2:37][CH3:38])(=[O:35])C>C(Cl)Cl.[Cl-].[Na+].O>[CH3:38][CH2:37][O:36][C:33]([CH:16]([CH:15]=[O:19])[CH2:21][O:8][CH2:7][CH:6]([CH:9]=[O:10])[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:35]

Komponenten

8

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22335286Ethyl acetate pentaneHCID 88418003HCID 88418003, Verbindung

Produkt 1

HCID 88418014(2-Ethoxycarbonyl)-(1-formyl)ethylene oxideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The procedure described by Evans and Williams European Patent Application No. 89302778.9, Publication No. 0334593 was employed for the Swern oxidation of (2-ethoxycarbonyl)-(1-hydroxymethyl) ethylene oxide (5.00 g) in methylene chloride (total 170 ml) with dimethylsulfoxide (7.3 mL), oxalyl chloride (4.2 mL) and triethylamine. Extractive work-up involving brine (150 mL), followed by trituration of impurities with pentane-ethyl acetate (2:1, 450 mL) afforded the title aldehyde (4.0 g, 80%). This material is used immediately and/or stored in dry methylene chloride at -25° C. under nitrogen.

Quellen und Nachweise

ORD-Eintrag
ord-f232e20708194e2e8e965bc431d16509
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169945

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