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

HRID 1379016Notes

Reaction equation

HRID 1379016 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c537816ec2fb43bda26016901e6d5b52
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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