Dimethylformamide → 3-Fluoroisonicotinaldehyde

HRID 7159

反応式

HRID 7159 の反応式
CN(CCN(C)C)C.C([Li])CCC.[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.CN([CH:24]=[O:25])C>C1COCC1>[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH:24]=[O:25]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 677943-FluoropyridineHCID 178418339Butyllithium

生成物 1

HCID 27630033-Fluoroisonicotinaldehyde収率 37.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of TMEDA (389 uL, 2.58 mmol) in THF (10 mL) at −78° C. was added a solution of n-butyl lithium in THF (2.5M, 1.03 mL, 2.58 mmol). After 30 minutes at −78° C., 3-fluoropyridine (221 uL, 2.57 mmol) was added. After another 2 hours at −78° C., DMF (219 uL, 2.83 mmol) was added. After a further 2 hours at −78° C., the reaction was quenched with saturated aqueous NaHCO3 (20 mL), extracted with ether (4×15 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the crude oil. Purification by column chromatography on silica gel (Hexanes: EtOAc 4:1) afforded the title compound as a pale yellow oil (120 mg, 37%). 1H NMR (CDCl3) 7.68 (t, 1H, J=5.2 Hz), 8.62 (d, 1H, J=4.7 Hz), 8.70 (s, 1H), 10.42 (s, 1H).

後処理

  1. waitAfter another 2 hours at −78° C.
  2. waitAfter a further 2 hours at −78° C.
  3. customthe reaction was quenched with saturated aqueous NaHCO3 (20 mL)
  4. extractionextracted with ether (4×15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude oil
  9. customPurification by column chromatography on silica gel (Hexanes: EtOAc 4:1)

出典と根拠

ORDレコード
ord-a94a42113b9747d29ec261a62954dea4
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

関連ノート

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