반응 #805994

반응 방정식

water

KOtBu

THF

N-(3-methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

N-(3-Methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

→

N-(3-methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

수율 60.2%

N-(3-Methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

수율 60.2%

용매

Et2O

Et2O

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for about 1 h
3. 3
   온도The mixture was warmed
4. 4
   온도to reflux overnight
5. 5
   workup.WAITthe layers were left
6. 6
   기타to separate
7. 7
   기타The aqueous layer was removed
8. 8
   여과the organic mixture was filtered
9. 9
   세척rinsing with Et2O
10. 10
    기타The solids were dried in vacuo

실험 절차

In a mechanically stirred 50 L vessel, Et2O (12.5 L) was added to methyltriphenylphosphonium bromide (1.81 kg, 5.06 mol). KOtBu (566 g, 5.06 mol) was added. The mixture was heated to reflux for about 1 h. THF (5 L) was added followed by addition of N-(3-methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (75) (475 g, 2.19 mol). The mixture was warmed to reflux overnight. The reaction was diluted with Et2O (5 L). The resulting mixture was cooled to rt and then poured into water (30 L). After stirring for about 1 h at rt, the layers were left standing to separate. The aqueous layer was removed and the organic mixture was filtered rinsing with Et2O. The solids were dried in vacuo to afford N-(3-methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (76) (284 g, 60% yield). 1H NMR (300 MHz, DMSO): δ 9.24 (s, 1H), 7.49 (s, 1H), 7.24 (s, 1H), 5.48 (m, 1H), 4.86 (m, 1H), 2.65 (m, 2H), 2.49 (m, 2H), 2.35 (s, 3H), 2.06 (s, 3H), 1.75 (m, 2H).

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