反応 #343739

反応方程式

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

収率 32.1%

溶媒

water

ether

ether

ether

反応条件

後処理

1. 1
   抽出extracted with ether
2. 2
   洗浄The extracts were washed with water
3. 3
   その他dried
4. 4
   濃縮concentrated
5. 5
   その他to give a solid
6. 6
   その他to be separated
7. 7
   その他the ether-soluble fraction (37.06 g) was chromatographed
8. 8
   その他to give
9. 9
   その他Crystallisation twice from methanol

実験手順

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.

出典