Acetic Anhydride → Ethyl ethoxymethyleneacetoacetate

HRID 542524Notizen

Reaktionsgleichung

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:10](OCC)(OCC)[O:11][CH2:12][CH3:13].C(OC(=O)C)(=O)C>>[CH2:12]([O:11][CH:10]=[CH:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Komponenten

Edukt 3

HCID 7918Acetic Anhydride

HCID 8868Ethyl Acetoacetate

HCID 31214Ethyl orthoformate

Produkt 1

HCID 54463595Ethyl ethoxymethyleneacetoacetateAusbeute 70 %

Versuchsvorschrift

Using the procedure of Crombie et al., Journ. of Chem. Soc. Perkin Trans. 1, 464-471 (1979), a solution of ethyl acetoacetate (26 g, 0.20 mol), triethyl orthoformate (29.6 g, 0.20 mol) and acetic anhydride (41 g, 0.40 mol) was refluxed for 90 minutes. Distillation under reduced pressure gave the product (1): 26 g, 70% yield; bp=85°-98° C. at 0.5 mm Hg (The following value is reported in the Crombie et al. publication: bp=85° C. at 0.25 mm Hg); NMR (CDCl3) δ 1.2-1.5 (m, 6H), 2.4-2.5 (d,3H), 4.0-4.6 (m,4H), 7.7 (d,1H). The signals were split into pairs of closely spaced lines indicative of the cis and trans isomers.

Aufarbeitung

distillationDistillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-b2a160b50ff64893a2277996949e7953
Quelldatensatz: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04657919

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