Synthesis of 3-(5-Alkyl-4-acetyl(ethoxycarbonyl))-2-propenoates from Derivatives of 3-Phenoxy-2-furylmethylene
1992 ◽
Vol 57
(8)
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pp. 1684-1692
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Keyword(s):
One Step
◽
3-(2-Furyl)propenoates IV-VIII were obtained by treatment of 5-phenoxy-2-furylmethylene derivatives I-III with alcoholic hydrogen chloride in one step. The probable transition mechanism of synthons I-III into the 2,4,5-trisubstituted furans is presented. The geometric isomers E-IV, Z-V and Z-VI, isolated in pure form, were transformed into the corresponding acids E-IX, Z-IX and E-X by base-catalyzed hydrolysis. Acid hydrolysis of the 1,3-diketone I afforded (4Z,6Z)-6-acetyl-7-hydroxy-2,4,6-octatrien-4-olide (XI). Structure of the products was verified by spectral (IR, UV, NMR and mass) methods.
1984 ◽
Vol 49
(8)
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pp. 1780-1787
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Keyword(s):
2010 ◽
Vol 59
(3)
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pp. 202-206
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1986 ◽
Vol 22
(10)
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pp. 1104-1107
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1995 ◽
Vol 60
(7)
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pp. 1196-1212
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Keyword(s):
1990 ◽
Vol 68
(11)
◽
pp. 2039-2044
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1960 ◽
Vol 2
(3)
◽
pp. 164-168
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