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

HRID 8497

반응식

HRID 8497 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6656788808ec4627bf81fed1d8c98130
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087618B2

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