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

HRID 10683노트

반응식

HRID 10683 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 219810662-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde수율 32%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-db9d400ae05d48d8a73cef95d7c4ce31
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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