反応式
C(=O)([O-])O[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>>[C:4]([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH:20][C:19]1[CH:21]=[CH:22][C:16]([C:15]([F:14])([F:23])[F:24])=[CH:17][CH:18]=1)#[CH:3]参加物
実験手順
The general procedure was followed with cinnamyl carbonate (0.094 g, 0.490 mmol) and p-trifluoromethylaniline (0.100 g, 0.62 mmol). The reaction was conducted at room temperature for 12 h. 1H NMR analysis of the crude reaction mixture indicated the ratio of regioisomers to be 94/6. The mixture was purified by flash column chromatography on silica gel (1% ethyl acetate in hexanes) to give the title compound (0.098 g, 72%). HPLC analysis indicated the enantiomeric excess of the product was 96% [Diacel CHIRALCEL OD-H (0.46 cm×25 cm); hexane/2-propanol=99.75/0.25; flow rate=0.6 mL/min; detection wavelength=254 nm; TR=29.8 (major), 34.9 (minor) min]: [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.50-7.35 (m, 7H), 6.64 (d, J=8.4 Hz, 2H), 6.08 (ddd, J=16.8, 10.4, 6.0 Hz, 1H), 5.33 (dt, J=7.2, 1.2 Hz, 1H), 5.30 (d, J=1.2 Hz, 1H), 5.02 (t, J=5.6 Hz, 1H), 4.40 (d, J=4.8 Hz, 1H). 13C NMR (100.59 MHz, CDCl3) δ 149.50, 140.88, 138.01, 128.88, 127.76, 127.08, 126.43 (q, J=3.8 Hz), 123.56, 119.03 (q, J=32.5 Hz), 116.58, 112.64, 60.34. Anal. Calcd for C16H14NF3: C, 69.31; H, 5.09; N, 5.05; F, 20.55. Found: C, 69.46; H, 5.12; N, 5.09; F, 20.37.
後処理
- custom1H NMR analysis of the crude reaction mixture
- customThe mixture was purified by flash column chromatography on silica gel (1% ethyl acetate in hexanes)
出典と根拠
- ORDレコード
- ord-685743d9e96b4111916b0516aabca118
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07732365B2
関連ノート
読み込み中…