1980
DOI: 10.1002/chin.198002326
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ChemInform Abstract: CHEMISTRY OF UNSATURATED ETHERS. XLVI. SYNTHESIS AND STEREOCHEMICAL STUDY OF ACETALS OF β,Γ‐UNSATURATED Δ‐HYDROXYALDEHYDES

Abstract: Wittig‐Reaktionen des Diethoxypropanals (IVb) mit Alkoxycarbonylmethylentriphenylphosphoranen liefern 25:75‐cis‐trans‐ Gemische der ungesättigten Ester (V); trans‐(Va) (Ausb. 37%) erhält man nach Horner durch Kondensation von (IVb) mit Carboethoxymethyldiethylphosphonat/NaH.

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“…While the rationale for our inability to acylate 6 or its ethers is not clear, we can readily make 1 from known acetal ester 7 [13], easily prepared from ethyl 3,3-diethoxypropionate (Scheme 3). Deprotonation of 4, followed by the addition of 7 and subsequent workup with 4M HCl afforded 1 plus dihydrofuran 8, which could be converted into 1 using PTSA.…”
Section: Scheme 1: Retrosynthetic Analysismentioning
confidence: 99%
“…While the rationale for our inability to acylate 6 or its ethers is not clear, we can readily make 1 from known acetal ester 7 [13], easily prepared from ethyl 3,3-diethoxypropionate (Scheme 3). Deprotonation of 4, followed by the addition of 7 and subsequent workup with 4M HCl afforded 1 plus dihydrofuran 8, which could be converted into 1 using PTSA.…”
Section: Scheme 1: Retrosynthetic Analysismentioning
confidence: 99%