4-Methylpyridine → 1-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

HRID 54937

반응식

HRID 54937 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC>O1CCCC1>[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](=[O:14])[CH2:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 79634-MethylpyridineHCID 8058HexaneHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one수율 86.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-methylpyridine (74.4 g) and ethyl 4-fluorobenzoate (134.4 g) in dry tetrahydrofuran (600 ml) was added a 1.0M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.6 l) dropwise with ice cooling. The mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added hexane (2.2 l) and the separated solid was collected, washed with hexane and dried. The obtained solid was dissolved in 3N-hydrochloric acid (800 ml) and the solution was neutralized with an aqueous saturated sodium bicarbonate solution. The separated solid was collected, washed with water and dried to give 1-(4-fluorophenyl)-2-(pyridin-4-yl)ethan-1-one (148 g).

후처리

  1. customthe separated solid was collected
  2. washwashed with hexane
  3. customdried
  4. dissolutionThe obtained solid was dissolved in 3N-hydrochloric acid (800 ml)
  5. customThe separated solid was collected
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-e20b73be0df544f7862a4b355c833ffe
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624931

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