3-Methoxyaniline → alpha-Ethynyl-N-(m-methoxyphenyl)-benzenemethanamine

HRID 14428

반응식

HRID 14428 반응식
C(=O)([O-])O[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1>>[C:4]([CH:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[CH:17]=1)#[CH:3]

참가 물질

3

반응물 2

HCID 108243-MethoxyanilineHCID 71446589Cinnamyl carbonate

생성물 1

HCID 86607480alpha-Ethynyl-N-(m-methoxyphenyl)-benzenemethanamine수율 82.6%

실험 절차

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and m-anisidine (0.150 g, 1.22 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 97/3. The mixture was purified by flash column chromatography on silica gel (4% ethyl acetate in hexanes) to give the title compound (0.192 g, 82%). [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.50-7.40 (m, 4H), 7.36 (tt, J=6.8, 2.0 Hz, 1H), 7.14 (t, J=8.0 Hz, 1H), 6.37 (dd, J=8.0, 2.4 Hz, 1H), 6.32 (dd, J=8.4, 2.0 Hz, 1H), 6.12 (ddd, J=16.8, 10.0, 6.0 Hz, 1H), 5.37 (dt, J=16.8, 1.4 Hz, 1H), 5.32 (dt, J=10.4, 1.4 Hz, 1H), 5.03 (br s, 1H), 4.18 (br s, 1H), 3.79 (s, 3H). 13C NMR (100.59 MHz, CDCl3) δ 160.50, 148.47, 141.68, 138.84, 129.71, 128.63, 127.35, 127.02, 115.98, 106.53, 102.62, 99.46, 60.71, 54.85. Anal. Calcd for C16H17NO: C, 80.30; H, 7.16; N, 5.85. Found: C, 80.17; H, 7.24; N, 5.78.

후처리

  1. custom1H NMR analysis of the crude reaction mixture
  2. customThe mixture was purified by flash column chromatography on silica gel (4% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-ddd0c858813145378e4c90d0ae00f598
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

연결된 노트

불러오는 중…