Sodium borohydride → 2,2-Difluoro-2-(pyridin-2-YL)ethanol

HRID 397471

반응식

HRID 397471 반응식
[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:3](OCC)=[O:4].[BH4-].[Na+]>C(O)C>[F:14][C:2]([F:1])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:3][OH:4]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10631894Ethyl difluoro(pyridin-2-yl)acetate

생성물 1

HCID 99422162,2-Difluoro-2-(pyridin-2-YL)ethanol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 19.5 g (97 mmol) of ethyl difluoro-2-pyridylacetate I-1-2 in 200 mL of absolute ethanol at 0° C. was added 4.42 g (116 mmol) of sodium borohydride in small portions. After 30 min, the reaction was quenched by the addition of 50 mL of sat. NH4Cl. The reaction mixture was concentrated at reduced pressure and the residue partitioned between 500 mL of ethyl acetate and sat. NaHCO3. The organic layer was washed with water, brine, and dried over Na2SO4 and concentrated at reduced pressure to give a brown oil that was purified on SiO2 (10×17 cm) using 1:1 EtOAc-hexane. After re-chromatographing the mixed fractions, all clean fractions were combined and concentrated at reduced pressure, giving I-1-3 as a beige crystalline solid: 1H NMR (CDCl3) δ3.6 (t, 1H), 4.17-4.3 (m, 2H), 7.4-7.45 (m, 1H), 7.73 (d, 1H), 7.84-7.91 (m, 1H), 8.61 (d, 1H).

후처리

  1. customthe reaction was quenched by the addition of 50 mL of sat. NH4Cl
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customthe residue partitioned between 500 mL of ethyl acetate and sat. NaHCO3
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated at reduced pressure
  7. customto give a brown oil that
  8. customwas purified on SiO2 (10×17 cm)
  9. concentrationconcentrated at reduced pressure
  10. customgiving I-1-3 as a beige crystalline solid

출처 및 근거

ORD 기록
ord-dc684ae29fcd44b7a46021a98d05aefa
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610701B2

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