Ethyl anisate → 2-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone

HRID 8497

反応式

HRID 8497 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:15]([C:14]2[CH:20]=[CH:21][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[O:16])[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 60979Ethyl anisateHCID 876016-Chloro-2-picolineHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 219922342-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a cold (0° C.) solution of 6-chloro-2-picoline (18.3 mL 166.5 mmol) and ethyl 4-methoxybenzoate (30.0 g, 166.5 mmol) in tetrahydrofuran (300 mL) was added lithium bis(trimethylsilyl)amide (333 mL, 1.0 M in tetrahydrofuran, 332.7 mmol) dropwise via a pressure equalizing funnel over 1 hour. Upon complete addition, the cold bath was removed and the resulting solution was heated at 45 ° C. for 15 hours. The mixture was cooled to room temperature, and the solution was concentrated. Methanol was added to quench the reaction, resulting in the formation of a yellow precipitate. The precipitate was collected by filtration and dried to give 2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone (37.4 g, 86%) as a yellow solid. 1H NMR (CDCl3): δ 7.99 (d, 2 H), 7.57 (t, 1 H), 7.22–7.19 (m, 2 H), 6.90 (d, 2H), 4.39 (s, 2H), 3.83 (s, 3 H); MS m/z 262 (M+1).

後処理

  1. customover 1 hour
  2. additionUpon complete addition
  3. customthe cold bath was removed
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationthe solution was concentrated
  6. additionMethanol was added
  7. customto quench
  8. customthe reaction
  9. customresulting in the formation of a yellow precipitate
  10. filtrationThe precipitate was collected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-6656788808ec4627bf81fed1d8c98130
出典データセット
uspto-grants-2006_08
特許番号
US07087618B2

関連ノート

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