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

HRID 410257노트

반응식

HRID 410257 반응식
[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

참가 물질

4

반응물 2

HCID 593269873-(2-Fluoropyridin-3-yl)cyclohex-2-enoneHCID 178418332HCID 178418332, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3fadeb295789443799b69cc779c307ea
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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