p-Toluidine → alpha-Ethynyl-N-(p-tolyl)-benzenemethanamine

HRID 14421

反応式

HRID 14421 の反応式
C(=O)([O-])O[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1>>[C:4]([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[CH:3]

参加物

3

反応物 2

HCID 7813p-ToluidineHCID 71446589Cinnamyl carbonate

生成物 1

HCID 86607474alpha-Ethynyl-N-(p-tolyl)-benzenemethanamine収率 76.6%

実験手順

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and p-toluidine (0.160 g, 1.5 mmol). The reaction was conducted at room temperature for 6 h. 1H NMR analysis of the crude reaction mixture indicated the ratio of regioisomers to be >99/1. The mixture was purified by flash column chromatography on silica gel (2% ethyl acetate in hexanes) to give the title compound (0.166 g, 76%). HPLC analysis indicated the enantiomeric excess of the product was 94% [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 ml; TR=24.2 (minor), 32.2 (major) min]: [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.44-7.32 (m, 4H), 7.28 (dt, J=7.2, 2.0 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.03 (t, J=7.2 Hz, 1H), 6.65 (t, J=7.2 Hz, 1H), 6.52 (d, J=8.0 Hz, 1H), 6.08 (ddd, J=16.8, 10.4, 6.0 Hz, 1H), 5.27 (dt, J=17.2, 1.2 Hz, 1H), 5.23 (dt, J=10.4, 1.2 Hz, 1H), 4.99 (t, J=4.4 Hz, 1 H), 3.88 (br s, 1H), 2.20 (s, 3H).

後処理

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

出典と根拠

ORDレコード
ord-13dce7e309d943cba17e75e749d0d6fc
出典データセット
uspto-grants-2010_06
特許番号
US07732365B2

関連ノート

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