반응 #805995

반응 방정식

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

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

hydroxy(tosyloxy)iodobenzene

NaCl

→

N-(3-methyl-6-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)acetamide

수율 68.1%

N-(3-Methyl-6-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)acetamide

수율 68.1%

용매

MeOH

water

MeOH

반응 조건

후처리

1. 1
   온도maintaining the internal temperature below about 20° C
2. 2
   workup.ADDITIONAfter completion of addition
3. 3
   추출The aqueous mixture was extracted with DCM (2×12 L)
4. 4
   세척The combined organic layers were washed with 5 N aqueous HCl (3.50 L)
5. 5
   건조dried with Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

In a 50 L mechanically stirred vessel, N-(3-methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (76) (710 g, 3.30 mol) was suspended in MeOH (22.5 L) and water (1.875 L). A solution of hydroxy(tosyloxy)iodobenzene (1.30 kg, 3.30 mol) in MeOH (3.50 L) was added maintaining the internal temperature below about 20° C. After completion of addition, the solution was stirred for about 15 min and then poured into saturated aqueous NaCl (35 L). The aqueous mixture was extracted with DCM (2×12 L). The combined organic layers were washed with 5 N aqueous HCl (3.50 L), dried with Na2SO4, filtered, and concentrated to afford N-(3-methyl-6-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)acetamide (77) (520 g, 68% yield). 1H NMR (300 MHz, DMSO): δ 9.24 (s, 1H), 7.20 (s, 1H), 6.98 (s, 1H), 3.68 (s, 2H), 2.88 (m, 2H), 2.52 (m, 2H), 2.16 (s, 3H), 2.04 (s, 3H), 1.82 (m, 2H).

출처