反应详情

A solution of 1-(3-benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one oxime (600 mg, 1.49 mmol) in 10 mL CHCl3 is cooled to −50° C. PCl5 (310 mg, 1.49 mmol) is added portionwise over 10 minutes to maintain the temperature below −30° C. The suspension is stirred until it becomes a solution then is warmed to RT and stirred for 2 hours. Water is added and the solution is extracted with CH2Cl2. The organic layer is washed with water, 5% NaOH and brine then is dried over MgSO4. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 14-100% EtOAc/hexane as eluent to give the title compound as a yellow solid. 1H NMR (CDCl3): 7.85-7.83 (d, J=8.59 Hz, 1H), 7.45-7.20 (m, 8H), 7.09-7.07 (d, J=7.58 Hz, 1H), 6.88-6.86 (dd, J=1.52 Hz, 8.34 Hz, 2 H), 5.80-5.79 (d, J=4.80 Hz, 1H), 5.22-5.14 (q, J=12.12, 2H), 4.74-4.69 (m, 1H), 3.37-3.32 (q, J=5.56 Hz, 1H), 3.19-3.08 (m, 2H), 3.04-2.97 (m, 1H), 2.81-2.65 (m, 2H). (M−1)−=401.

1. temperatureto maintain the temperature below −30° C
2. stirringstirred for 2 hours
3. extractionthe solution is extracted with CH2Cl2
4. washThe organic layer is washed with water, 5% NaOH and brine
5. dry with materialthen is dried over MgSO4
6. customThe solvent is removed under reduced pressure
7. customthe residue is purified by flash chromatography