تفاعل #91893

معادلة التفاعل

5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzene-1-sulfonate

1,2,3,4-tetrahydroquinoline

BINAP

Cs2CO3

→

title compound

المردود 76.4%

6-(1,2,3,4-tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-one

المردود 76.4%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux under nitrogen overnight
3. 3
   ترشيحThe mixture was filtered
4. 4
   تركيزconcentrated
5. 5
   أخرىthe residue was purified by silica gel chromatography (10% EtOAc/hexanes)

الإجراء التجريبي

To a solution of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzene-1-sulfonate (1.0 g, 3.4 mmol) in THF (20 mL) was added 1,2,3,4-tetrahydroquinoline (0.55 g, 4.1 mmol), Pd(OAc)2 (92 mg, 0.41 mmol), BINAP (383 mg, 0.61 mmol) and Cs2CO3 (1.7 g, 5.1 mmol). The mixture was heated to reflux under nitrogen overnight. The mixture was filtered and concentrated, and the residue was purified by silica gel chromatography (10% EtOAc/hexanes) to give 0.72 g (76%) of the title compound as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.94 (d, J=8.4 Hz, 1H), 7.18-7.04 (m, 4H), 6.97 (d, J=2.4 Hz, 1H), 6.90 (dt, J=7.6 Hz, 1.2 Hz, 1H), 3.69 (t, J=6.0 Hz, 2H), 2.87 (t, J=6.0 Hz, 2H), 2.77 (t, J=6.4 Hz, 2H), 2.61 (t, J=6.4 Hz, 2H), 2.14-2.08 (m, 2H), 2.05-1.98 (m, 2H). [M+H] calc'd for C19H19NO, 278. found 278.

المصدر