HCID 86697887、化合物 → 1-(5-Fluorothiophen-2-yl)ethan-1-one

HRID 1618972ノート

反応式

HRID 1618972 の反応式
[F:1][C:2]1[S:6][C:5]([C:7](N(OC)C)=[O:8])=[CH:4][CH:3]=1.[CH3:13][Mg]Br>O1CCCC1>[F:1][C:2]1[S:6][C:5]([C:7](=[O:8])[CH3:13])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 86697887HCID 86697887、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 217320781-(5-Fluorothiophen-2-yl)ethan-1-one収率 103.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-fluoro-N-methoxy-N-methylthiophene-2-carboxamide (12.34 g, 65.2 mmol) in tetrahydrofuran (163 mL) at 0° C. under nitrogen is added methyl magnesium bromide (3 M solution in tetrahydrofuran, 32.6 mL, 97.8 mmol) over a period of 25 minutes, while maintaining the internal temperature below 10° C. The cooling bath is removed and the solution is allowed to warm to room temperature over 1 hour. A saturated solution of ammonium chloride (200 mL) is added and the mixture is stirred for 10 minutes. The mixture is diluted with diethyl ether (200 mL) and the phases are separated. The aqueous phase is re-extracted with diethyl ether (2×150 mL) and the combined organic extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure (keeping the water bath below 25° C.) to give the crude title compound (9.70 g, 103%) as a pale amber liquid. 1H NMR (CDCl3) δ 2.47 (s, 3H), 6.53 (dd, J=1.2, 4.3 Hz, 1H), 7.38 (t, J=4.0 Hz, 1H).

後処理

  1. temperaturewhile maintaining the internal temperature below 10° C
  2. customThe cooling bath is removed
  3. additionA saturated solution of ammonium chloride (200 mL) is added
  4. additionThe mixture is diluted with diethyl ether (200 mL)
  5. customthe phases are separated
  6. extractionThe aqueous phase is re-extracted with diethyl ether (2×150 mL)
  7. dry with materialthe combined organic extracts are dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (
  10. customthe water bath below 25° C.

出典と根拠

ORDレコード
ord-b049a6cf6dcb463bba99eb1430b21181
出典データセット
uspto-grants-2014_07
特許番号
US08772282B2

反応ノート

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