5-Cyano-2-fluorobenzaldehyde → 4-Fluoro-3-(1-hydroxyethyl)benzonitrile

HRID 398357노트

반응식

HRID 398357 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])#[N:2].[CH3:12][Li]>C1COCC1>[F:11][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:10][C:7]=1[CH:8]([OH:9])[CH3:12]

참가 물질

4

반응물 2

HCID 109097255-Cyano-2-fluorobenzaldehydeHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 230001664-Fluoro-3-(1-hydroxyethyl)benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-cyano-2-fluorobenzaldehyde (1.50 g, 10.06 mmol) in THF (15 mL) cooled to 0° C. was added methyllithium (7.90 mL, 11.06 mmol). The mixture was stirred at room temperature for 2 h and quenched by the addition of saturated NH4Cl (10 mL). The mixture was partitioned between ethyl acetate (50 mL) and water (20 mL), the organic was washed with water (20 mL), dried over magnesium sulfate and concentrated in vacuo to provide a residue. Purification via flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2) afforded pure compound:

후처리

  1. customquenched by the addition of saturated NH4Cl (10 mL)
  2. customThe mixture was partitioned between ethyl acetate (50 mL) and water (20 mL)
  3. washthe organic was washed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto provide a residue
  7. customPurification
  8. washvia flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2)
  9. customafforded pure compound

출처 및 근거

ORD 기록
ord-78c9206df81240b7876af20d7576b8a9
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610692B1

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