Pyrrolidine → 2-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde

HRID 10683ノート

反応式

HRID 10683 の反応式
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:3]=1[CH:4]=[O:5].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)(=O)C>[N:15]1([C:2]2[CH:9]=[CH:8][C:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

4

反応物 2

HCID 31268PyrrolidineHCID 167686562-Fluoro-5-(thiophen-2-yl)benzaldehyde

生成物 1

HCID 219810662-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde収率 32%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Ex-63A: A solution of 2-fluoro-5-thiophen-2-yl-benzaldehyde (1.42 g, 6.89 mmol) in pyrrolidine was refluxed (10 mL). After 4.5 days the reaction mixture was cooled and diluted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate, dried over sodium sulfate, and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (20%, v/v, in hexane) afforded 2-pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde (0.5 g, 32%). 1H NMR (CDCl3) δ 10.14 (s, 1H), 7.94 (d, J=2 Hz, 1H), 7.62 (dd, J=2.7, 9 Hz, 1H), 7.22–7.20 (m, 2H), 7.07–7.04 (m, 1H), 6.86 (d, J=9 Hz, 1H), 3.41 (m, 4H), 2.01 (m, 4H).

後処理

  1. temperatureAfter 4.5 days the reaction mixture was cooled
  2. washThe solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washElution with ethyl acetate (20%, v/v, in hexane)

出典と根拠

ORDレコード
ord-db9d400ae05d48d8a73cef95d7c4ce31
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

反応ノート

読み込み中…