Ethylamine → (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide

HRID 749457ノート

反応式

HRID 749457 の反応式
[CH2:1]([NH2:3])[CH3:2].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH2:15][CH:16]=[CH2:17])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1>C(Cl)Cl>[CH2:1]([NH:3][C:12](=[O:13])[C@H:11]([C:8]1[CH:7]=[CH:6][C:5]([F:4])=[CH:10][CH:9]=1)[CH2:15][CH:16]=[CH2:17])[CH3:2]

参加物

4

反応物 2

HCID 6341EthylamineHCID 15536025(S)-2-(4-fluorophenyl)pent-4-enoyl chloride

生成物 1

HCID 68978786(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide収率 59%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A stream of ethylamine was introduced to ice-cooled CH2Cl2 (5 mL) until 350 mg gas had been consumed. A solution of (2S)-2-(4-fluorophenyl)pent-4-enoyl chloride (0.24 g in 5 mL of CH2Cl2, 1.1 mmol) was added dropwise. The mixture was stirred at room temperature for 1 h and then diluted with CH2Cl2 (10 mL). The solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M) and then brine. The organic solution was dried over Na2SO4 and then the solvent was evaporated. There was obtained 0.15 g (59%) of (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide. 1H NMR (500 MHz, CDCl3): 1.1 (t, 3H), 2.5 (m, 1H), 2.8-3.0 (m, 2H), 3.2-3.4 (m, 3H), 5.0-5.1 (m, 2H), 5.6-5.8 (m, 1H), 7.0 (t, 2H), 7.3 (m, 2H).

後処理

  1. customhad been consumed
  2. washThe solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-dbc78ff35b2941078b77e2bcd200f3c8
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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