3-(2-Fluoropyridin-3-yl)cyclohex-2-enone → (Rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol

HRID 410257ノート

反応式

HRID 410257 の反応式
[CH3:1][Mg]Cl.[F:4][C:5]1[C:10]([C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1>C1COCC1>[F:4][C:5]1[C:10]([C:11]2[CH2:16][CH2:15][CH2:14][C:13]([CH3:1])([OH:17])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1

参加物

4

反応物 2

HCID 593269873-(2-Fluoropyridin-3-yl)cyclohex-2-enoneHCID 178418332HCID 178418332、化合物

生成物 1

HCID 67416977(Rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 3.0 M solution of methylmagnesium chloride in tetrahydrofuran (4.88 mL, 14.64 mmol) was added slowly to a solution of 3-(2-fluoropyridin-3-yl)cyclohex-2-enone (2.00 g, 10.46 mmol) in THF (20 ml) at −78° C. After completion of the addition the reaction mixture was stirred overnight while it gradually warmed up to RT. It was cooled in an ice water bath and distilled water (5 ml) was added slowly. The mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate (200 ml) was added, and it was extracted EtOAc (3×100 ml). The combined organic layers were washed by brine and dried over sodium sulfate. Filtration and concentration under reduced pressure gave (rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol as a light yellow liquid. MS (ESI, pos. ion) m/z: 208.0 (M+1).

後処理

  1. additionAfter completion of the addition the reaction mixture
  2. temperatureIt was cooled in an ice water bath
  3. distillationdistilled water (5 ml)
  4. additionwas added slowly
  5. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate (200 ml)
  6. additionwas added
  7. extractionit was extracted EtOAc (3×100 ml)
  8. washThe combined organic layers were washed by brine
  9. dry with materialdried over sodium sulfate
  10. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-3fadeb295789443799b69cc779c307ea
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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