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

HRID 398357ノート

反応式

HRID 398357 の反応式
[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]

参加物

4

反応物 2

HCID 109097255-Cyano-2-fluorobenzaldehydeHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-78c9206df81240b7876af20d7576b8a9
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

反応ノート

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