반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2([C:11]#N)[CH2:10][CH2:9][CH2:8]2)=[C:4](I)[CH:3]=1.C([Li])(C)(C)C.C1C[O:24]CC1>>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([CH2:6][C:7]3([CH2:10][CH2:9][CH2:8]3)[C:11]2=[O:24])=[CH:4][CH:3]=1참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
A dried flask charged with 1-(4-bromo-2-iodobenzyl)cyclobutanecarbonitrile (Intermediate 37, 2.60 g, 6.91 mmol), was dissolved in dry THF (100 mL) under an argon atmosphere. The resulting mixture was cooled to −78° C. and then was tert-butyllithium (1.7 M in pentane, 8.13 mL, 13.83 mmol), added dropwise. The reaction was stirred for 1.5 h at −78° C. and then the reaction was quenched with MeOH (0.5 mL), followed by aq. hydrochloric acid (2M, 10 mL). The resulting solution was concentrated to remove the organic solvent and then partitioned between DCM and water. The organic phase was dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (eluent: heptane/EtOAc20:1-15:1-10:1) to afford the title compound (1.1 g, 63% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.97-2.13 (m, 3 H), 2.13-2.24 (m, 1 H), 2.45-2.60 (m, 2 H), 3.24 (s, 2 H), 7.31 (d, 1 H), 7.67 (dd, 1H), 7.88 (d, 1 H); GC MS (EI) m/z 250 M
후처리
- additionadded dropwise
- customthe reaction was quenched with MeOH (0.5 mL)
- concentrationThe resulting solution was concentrated
- customto remove the organic solvent
- custompartitioned between DCM and water
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated
- customto give a crude product which
- customwas purified by flash chromatography (eluent: heptane/EtOAc20:1-15:1-10:1)
출처 및 근거
- ORD 기록
- ord-89dec8f81d7b444bb4cd4db58a0eeedf
- 출처 데이터셋
- uspto-grants-2013_04
- 특허 번호
- US08415483B2
연결된 노트
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