Benzoic acid, 4-fluoro-, ethyl ester → 2-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one

HRID 723983ノート

反応式

HRID 723983 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([C:14](OCC)=[O:15])=[CH:12][CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:14]([C:13]2[CH:19]=[CH:20][C:10]([F:9])=[CH:11][CH:12]=2)=[O:15])[CH:3]=1

参加物

5

反応物 3

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 5813924-Chloro-2-methylpyridineHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 218740612-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (020 C.) solution of 4-chloro-2-picoline (5.0 g, 39 mmol) and ethyl 4-fluorobenzoate (6.6 g, 39 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (80 mL, 1.0 M in tetrahydrofuran, 80 mmol) dropwise via a pressure equalizing funnel over 30 minutes. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure and methanol was added to the reaction, resulting in the formation of a white precipitate. The precipitate was collected by filtration and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 99%) as a white solid. 1H-NMR (DMSO-d6): δ 7.90 (m, 3H), 7.11 (t, 2H), 6.56 (s, 1H), 5.67 (s, 1H), 4.14 (m, 2H); 19F-NMR (DMSO-d6): δ −115.67; MS m/z 250 (M+1).

後処理

  1. customover 30 minutes
  2. additionUpon complete addition
  3. customthe cold bath was removed
  4. concentrationThe reaction mixture was concentrated under reduced pressure and methanol
  5. additionwas added to the reaction
  6. customresulting in the formation of a white precipitate
  7. filtrationThe precipitate was collected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-7b5a98b2b24a481abfca0aff71a5de67
出典データセット
uspto-grants-2006_11
特許番号
US07141569B2

反応ノート

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