2,4,6-Trimethylaniline → alpha-Ethynyl-N-(2,4,6-trimethylphenyl)-benzenemethanamine

HRID 14423

반응식

HRID 14423 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][C:15]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:16]=1[NH2:17]>>[C:4]([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH:17][C:16]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=1[CH3:14])#[CH:3]

참가 물질

3

반응물 2

HCID 69132,4,6-TrimethylanilineHCID 71446589Cinnamyl carbonate

생성물 1

HCID 86607476alpha-Ethynyl-N-(2,4,6-trimethylphenyl)-benzenemethanamine수율 85%

실험 절차

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and 2,4,6-trimethylaniline (0.170 g, 1.25 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 (1% ethyl acetate in hexanes) to give the title compound (0.207 g, 85%). 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=17.0 (major), 19.5 (minor) min]: [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.38-7.23 (m, 5H), 6.78 (s, 2H), 6.05 (ddd, J=17.2, 10.0, 6.4 Hz, 1H), 5.25 (dt, J=16.8, 1.6 Hz, 1H), 5.17 (dt, J=10.4, 1.3 Hz, 1H), 4.61 (t, J=6.4 Hz, 1H), 3.12 (br s, 1H), 2.22 (s, 3H), 2.11 (s, 6H). 13C NMR (100.59 MHz, CDCl3) δ 142.92, 141.89, 139.34, 130.89, 129.77, 129.34, 128.41, 127.10, 126.93, 115.51, 64.19, 20.56, 18.61. Anal. Calcd for C18H21N: C, 86.01; H, 8.42; N, 5.57. Found: C, 86.18; H, 8.49; N, 5.62.

후처리

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

출처 및 근거

ORD 기록
ord-5acc5f972aa7412daac73046d4b1f8af
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

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