Tetrahydrofuran → Isopropanol hydrochloride
反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=3)[CH2:12]2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:23]1COCC1>>[CH3:23][CH:8]([OH:9])[CH3:4].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:10][CH:11]2[CH2:12][C:13]3[C:18](=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][CH:14]=3)[CH2:19]2)[CH:5]=[CH:6][CH:7]=1参加物
4
反応条件
- 温度
- 0 °C
実験手順
To 2-((3-chlorophenyl)carbonyl)amino-5-nitroindane (2.2 g, 7.0 mmol) in THF (75 ml) was added BH3 ·THF (1.0M, 35 ml, 35 mmol) dropwise. The mixture was refluxed for 12 hr, cooled to 0° C., quenched with 4N HCl (60 ml), and refluxed for 1 hr. The resulting solution was evaporated to an oil, made basic with 50% NaOH, and extracted with methylene chloride (3×20 ml). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated to an oil. Treatment with IPA/HCl yielded 2-((3-chlorophenyl)methyl)amino-6-nitroindane: (2.1 g, 88% two steps); m.p. 234°-237° C.