23262-34-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 1481, 1978 DOI: 10.1021/ja00473a025Tetrahedron Letters, 22, p. 4489, 1981 DOI: 10.1016/S0040-4039(01)93022-9

InChI:InChI=1/C15H22O/c1-13(2)6-4-7-14(3)8-5-9-15-10-11-16-12-15/h6,8,10-12H,4-5,7,9H2,1-3H3/b14-8+

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 81719-68-8 (3-furylmethyl)magnesium bromide 
• 85757-86-4 (furan-3-ylmethyl)magnesium chloride 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 63184-61-2 3-(bromomethyl)furan 

Downstream Products

• 92631-16-8 9-(3-furyl)-2,6-dimethyl-3-phenylthionona-1,6(E)-diene 

Relevant academic research and scientific papers

Selective Alkylation and Allylation of Allylic Halides by Tetraorganoidates: Regio- and Stereo-selective Synthesis of Rosefuran and Sesquirosefuran

Tetraalkylindanes regioselectively alkylate allylic bromides at the α-carbon.In this way, 1,5-dienes have been regio- and stereo-selectively synthesized by the allyl-allyl coupling of allylic bromides and allylic indates, including rosefuran 1 and sequirosefuran 3.

REGIO-CONTROLLED PRENYLATION AND GERANYLATION OF 3-FURYLMETHYLMAGNESIUM BROMIDE. SELECTIVE SYNTHESES OF 3-SUBSTITUTED FURANOID AND 2-SUBSTITUTED 3-METHYLFURANOID TERPENES.

Coupling reactions of 3-furylmethylmagnesium bromide with prenyl and geranyl diethyl phosphates gave 2-substituted 3-methylfurans, rosefuran and sesquirosefuran, as the main products. When the reactions were carried out in the presence of a catalytic amount of copper(I) iodide, normal coupling occurred and 3-substituted furans, perillene and dendrolasin, were formed in good yields. The related naturally occurring 3-substituted thiophene, 3-(4-methyl-3-pentenyl)thiophene, was also synthesized from 3-thienylmethylmagnesium bromide and prenyl diethy phosphate.

SELECTIVE SYNTHESES OF DENDROLASIN AND SESQUIROSEFURAN BY THE COUPLING OF 3-FURYLMETHYLMAGNESIUM BROMIDE WITH GERANYL DIETHYL PHOSPHATE

Coupling reaction of 3-furylmethylmagnesium bromide with geranyl diethyl phosphate in the presence and the absence of copper(I) iodide affords dendrolasin and sesquirosefuran, respectively, in ca. 80 percent selectivity

A SIMPLE SYNTHESIS OF 3-SUBSTITUTED FURANS. THE PREPARATIONS OF DENDROLASIN, PERILLENE AND CONGENERS

The Grignard reagent 7, derived from 3-chloromethyl furan, reacts with various alkyl- and allylic halides, in the presence of Li2CuCl4, to provide high yields of 3-substituted furans.