Hydrochloric Acid → 1-(4-Fluorophenyl)-2-(2-fluoropyridin-4-yl)ethanone

HRID 23519

反応式

HRID 23519 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1.[F:19][C:20]1[CH:30]=[CH:29][C:23]([C:24](OCC)=[O:25])=[CH:22][CH:21]=1.Cl.[OH-].[Na+]>>[F:19][C:20]1[CH:30]=[CH:29][C:23]([C:24](=[O:25])[CH2:18][C:16]2[CH:15]=[CH:14][N:13]=[C:12]([F:11])[CH:17]=2)=[CH:22][CH:21]=1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27374032-Fluoro-4-methylpyridine

生成物 1

HCID 110317691-(4-Fluorophenyl)-2-(2-fluoropyridin-4-yl)ethanone

実験手順

To a solution of sodium bis(trimethylsilyl)amide (0.465 L, 1M) in TBF (765 mL) under nitrogen, cooled to 2° C., was added 2-fluoro-4-methylpyridine (25 g, 0.225 mol) and the solution stirred for 45 minutes in an ice bath. Ethyl 4-fluoro-benzoate (35 mL, 0.239 mol) was added and the reaction was stirred for 1.5 hours at RT. The reaction mixture was poured into excess aqueous 2N HCl, and the aqueous layer was made basic with 5 N NaOH and extracted with EtOAc. The organic extracts were combined, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and filtered through a cotton plug. Hexanes were added and the CH2Cl2 was removed under reduced pressure until precipitation of the title compound occurred as a pale yellow solid (43.2 g).

後処理

  1. stirringthe reaction was stirred for 1.5 hours at RT
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. filtrationfiltered through a cotton plug
  9. additionHexanes were added
  10. customthe CH2Cl2 was removed under reduced pressure until precipitation of the title compound

出典と根拠

ORDレコード
ord-8b2ce258c09b4c8d8cddd43a27d5f774
出典データセット
uspto-grants-2005_02
特許番号
US06852727B2

関連ノート

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