99054-37-2

Upstream product

• 54362-87-7 6-chloro-3-oxohexanoic acid ethyl ester 
• 217474-02-7 ethyl 6-hydroxy-2-hexynoate 
• 83925-49-9 CH₃COCH₂CO₂C₂H₃^(2-)*2Li⁽¹⁺⁾ 
• 107-04-0 1-Bromo-2-chloroethane 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 866216-67-3 ethyl (dihydro-furan-2(3H)-ylidene)-(2,4-dimethoxy-phenyl)acetate 
• 2434-02-8 ethyl tetrahydrofuran-2-acetate 
• 805228-93-7 ethyl (Z)-2-bromo-2-[4,5-dihydrofuran-2(3H)-ylidene]acetate 
• 4915-21-3 ethyl 2-furanacetate 
• 805251-01-8 6-bromo-3-oxohexanoic acid ethyl ester 

Relevant academic research and scientific papers

Regio- and diastereoselective synthesis of 2-alkylidenetetrahydrofurans by domino SN/SN′ and SN/SN reactions of 1,3-dicarbonyl dianions

The domino C,O-cyclodialkylation reaction of dilithiated 1,3-dicarbonyl compounds with 1,4-dibromo-2-butene resulted in regio- and diastereoselective formation of 2-alkylidene-5-vinyltetrahydrofurans. The cyclization of 1,3-dicarbonyl dianions with 1-brom

TBAF-catalyzed cyclization of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates

Tetrabutyl ammonium fluoride (TBAF) was found to be capable of catalyzing the intramolecular hydroalkoxylation of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates. The reaction could be used to prepare 2,5-substituted THF rings and 2,6-substituted THP rings.

Efficient synthesis of furan-2-ylacetates, 7-(alkoxycarbonyl)benzofurans, and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans based on cyclization reactions of free and masked dianions: A "cyclization/dehydrogenation" strategy

A variety of furan-2-ylacetates have been prepared by dehydrogenation of monocyclic 2-alkylidene-tetrahydrofurans, which are readily available by cyclizations of open-chained 1,3-dicarbonyl dianions with 1-bromo-2- chloroethane. 5′H-[2,3′]Bifuranyl-2′-one

Synthesis of benzofurans with remote bromide functionality by domino "ring-cleavage-deprotection-cyclization" reactions of 2-alkylidenetetrahydrofurans with boron tribromide

Bromination and subsequent Suzuki reactions of 2- alkylidenetetrahydrofurans, readily available by [3+2] cyclizations, afforded 1′-(2″-methoxyphenyl)-2-alkylidenetetrahydrofurans. Treatment of the latter with boron tribromide and subsequent addition of wa

Functionalization of 2-alkylidenetetrahydrofurans and 2- alkylidenepyrrolidines by palladium(0)-catalyzed cross-coupling reactions

2-Alkylidenetetrahydrofurans and 2-alkylidenepyrrolidines were efficiently functionalized by bromination of the exocyclic double bond and subsequent palladium-catalyzed cross-coupling reactions.

Chemoselective, Regioselective, and E/Z-Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Sequential Reactions of Ambident Dianions and Monoanions

A number of novel β-ketoesters were prepared by regioselective alkylation reactions of simple β-ketoester dianions. The cyclization of the dianions of these 1,3-dicarbonyl derivatives with 1-bromo-2-chloroethane afforded a variety of 2-alkylidenetetrahydr

Regio- and Stereoselective Synthesis of 2-Alkylidene-hydrofurans by Domino-Cyclodialkylations of 1,3-Dicarbonyl-Dianions with 1-Bromo-2-chloroethane

Reaction of 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane results in regio- and stereoselective formation of 2-alkylidene-hydrofurans.

Application of the Intramolecular Aza-Wittig Reaction to the Synthesis of Vinylogous Urethanes and Amides

The treatment of ω-azido β-dicarbonyl derivatives with 1 equiv of triphenylphosphine leads to a transient phosphinimine (Staudinger reaction), which cyclizes into vinylogous urethanes and amides via an intramolecular aza-Wittig reaction in excellent yields.The starting azides were obtained by a nucleophilic substitution by NaN3 in Me2SO on the corresponding ω-halo β-dicarbonyl derivatives that were accessible by the γ-alkylation of β-dicarbonyl compounds with α,ω-dihaloalkanes.