반응 #738032

반응 방정식

6-bromo-2-heptyloxynaphthalene

methyl acrylate

tri-o-tolylphosphine

→

Methyl (E)-3-(6-heptyloxynaphth-2-yl)acrylate

용매

triethylamine

반응 조건

후처리

1. 1
   온도is refluxed for 16 hours
2. 2
   온도The reaction mixture is then cooled
3. 3
   기타is partitioned between ethyl acetate and water
4. 4
   세척the organic phase is washed with water
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated down
8. 8
   기타The residue is chromatographed over 250 g of silica gel
9. 9
   기타crystallized from toluene

실험 절차

A mixture of 5.2 g of 6-bromo-2-heptyloxynaphthalene, 25 ml of triethylamine, 4.3 ml of methyl acrylate, 0.072 g of palladium acetate and 0.392 g of tri-o-tolylphosphine is refluxed for 16 hours. The reaction mixture is then cooled and is partitioned between ethyl acetate and water and the organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated down. The residue is chromatographed over 250 g of silica gel using toluene/ethyl acetate (3:1) and then crystallized from toluene. This gives methyl (E)-3-(heptyloxynaphth-2-yl)acrylate.

출처