反应详情

Sodium hydride (48 mg, 1.2 mmol) was added to a solution of 30 (300 mg, 0.8 mmol) in THF (10 ml) and the reaction mixture was stirred at rt for 20 min. 2-Iodopropane (0.12 ml, 1.2 mmol) was added and the reaction mixture was stirred at rt for 26 h. Further 2-iodopropane (0.36 ml, 3.6 mmol) was added and the reaction mixture was heated at 60° C. 24 h. The solution was concentrated in vacuo, water was added and the aqueous layer was extracted with ethyl acetate (3×). The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 50 g, 100% hex-100% EtOAc over 35 min) afforded the title compound (259 mg, 77%) as a colourless oil; 1H NMR (270 MHz; CDCl3) 1.31 (6H, d, J=6.2 Hz, 2×CH3), 2.66-2.75 (4H, m, 2×CH2), 3.54 (2H, s, CH2), 3.62 (2H, s, CH2), 3.80 (3H, s, OCH3), 4.54 (1H, septet, J=6.2 Hz, CH), 5.09 (2H, s, CH2Ph), 6.50 (1H, s, CH), 6.61 (1H, s, CH), 6.77-6.81 (1H, m, CH), 6.91-6.94 (2H, m, 2×CH), 7.16-7.47 (6H, m, 5×CH, phenyl). 13C NMR (67.5 MHz; CDCl3) 22.18 (CH3), 28.77 (CH2), 50.80 (CH2), 55.85 (CH2), 56.16 (OCH3), 62.85 (CH2), 69.75 (CH), 71.18 (CH2), 110.13 (CH), 114.30 (CH), 114.59 (CH), 116.47 (CH), 126.31 (C), 127.35 (CH), 127.55 (C), 127.82 (CH), 128.58 (CH), 129.32 (CH), 137.40 (C), 140.16 (C), 146.69 (C), 147.91 (C), 158.02 (C). LC/MS (APCI−) tr=7.47 min, m/z 416.35 (M−H)−.

1. stirringthe reaction mixture was stirred at rt for 26 h
2. temperaturethe reaction mixture was heated at 60° C
3. custom24 h
4. concentrationThe solution was concentrated in vacuo, water
5. additionwas added
6. extractionthe aqueous layer was extracted with ethyl acetate (3×)
7. washThe combined organic phases were washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customPurification (flashmaster: 50 g, 100% hex-100% EtOAc over 35 min)