반응 #343739

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3-formylfuran

( E )-

methyl 3-methoxy-2-(3-phenoxymethyl-2-thienyl)propenoate

3-styrylfuran

methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate

triphenylphosphine oxide

Potassium tert-butoxide

phosphonium

→

(E)-3-styrylfuran

수율 32.1%

용매

water

ether

ether

ether

반응 조건

후처리

1. 1
   추출extracted with ether
2. 2
   세척The extracts were washed with water
3. 3
   기타dried
4. 4
   농축concentrated
5. 5
   기타to give a solid
6. 6
   기타to be separated
7. 7
   기타the ether-soluble fraction (37.06 g) was chromatographed
8. 8
   기타to give
9. 9
   기타Crystallisation twice from methanol

실험 절차

Potassium tert-butoxide (35.7 g) was added in one portion to a stirred suspension of benzyltriphenylphosphonium chloride (41.6 g) in ether (1 liter). After 1 hour, a solution of 3-formylfuran (17.5 g) in ether (60 ml) was added to the resulting orange mixture which was then stirred for 2 hours, poured into water, and extracted with ether. The extracts were washed with water, dried and concentrated to give a solid. Trituration of this solid with ether enabled much of the weakly-soluble triphenylphosphine oxide and excess phosphonium salt to be separated, and the ether-soluble fraction (37.06 g) was chromatographed using ether as eluent to give a mixture of (E)- and (Z)-isomers of 3-styrylfuran (27 g) as a yellow solid. Crystallisation twice from methanol gave (E)-3-styrylfuran (5.12 g), mp 96° C., as a yellow solid.

출처