Dimethylformamide → 6-(2-Methylphenyl)pyridine-3-carbaldehyde

HRID 493392ノート

反応式

HRID 493392 の反応式
[Li][CH2:2]CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C[N:13]([CH:15]=O)[CH3:14].[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[C:8]1([CH3:2])[CH:7]=[CH:6][CH:11]=[CH:10][C:9]=1[C:15]1[CH:21]=[CH:17][C:18]([CH:19]=[O:20])=[CH:14][N:13]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8058HexaneHCID 178418339Butyllithium

生成物 1

HCID 247296626-(2-Methylphenyl)pyridine-3-carbaldehyde収率 91%

反応条件

温度
-40 °C

実験手順

To a stirred solution of 125 mg of the above compound (0.50 mmol)in THF (2.0 mL) under argon at −74° C. was added 220 μL of nBuLi solution in hexane (2.5 M, 0.55 mmol, 1.1 eq) over 5 min, the temperature not allowed to rise above −71° C. A light green solution formed, which became dark green after 30 min. After 45 min, 49.4 μL (0.61 mmol, 1.2 eq) of DMF was added and the reaction allowed to warm to −40° C. After 14 h, a bright orange solution had formed. The reaction was quenched with 10% citric acid and the mixture stirred rapidly for 20 min at room temperature. The resulting bright yellow solution was extracted twice with EtOAc. The organic extracts were combined, dried over MgSO4, filtered and concentrated to give a yellow oil. The crude mixture thus obtained was purified by silica gel chromatography using ethyl acetate/dichloromethane (1:24) as eluant, (2.5×10 cm column), to give white solid, mp 82-84° C., 90.3 mg, 91% yield.

後処理

  1. customto rise above −71° C
  2. customA light green solution formed
  3. waitAfter 45 min
  4. waitAfter 14 h
  5. customa bright orange solution had formed
  6. customThe reaction was quenched with 10% citric acid
  7. extractionThe resulting bright yellow solution was extracted twice with EtOAc
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow oil

出典と根拠

ORDレコード
ord-3eabd6db867742d2b37abad8c0eea57a
出典データセット
uspto-grants-2009_05
特許番号
US07534763B2

反応ノート

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