4-Fluorophenol → HCID 22612275, compound

HRID 844071Notes

Reaction equation

HRID 844071 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H][H].F[C:14]1[C:19]([C:20](=[O:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=[CH:16][N:15]=1>CCCCC.CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[C:19]([C:20](=[O:29])[CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 97324-FluorophenolHCID 24758Sodium hydride2×HCID 22612323HCID 22612323, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22612275HCID 22612275, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
80 °C

Procedure

To the sodium hydride obtained by washing 351 mg (7.73 mmol) of 50% sodium hydride dispersion in mineral oil with pentane was added 10 mL of dimethylformamide followed by 867 mg (7.73 mmol) of p-fluorophenol. After the hydrogen evolution ceased, 886 mg (3.87 mmol) 1-(2-Fluoro-pyridin-3-yl)-3-phenyl-propan-1-one was added dissolved in a minimum amount of DMF. The mixture was heated to 80° C. for 3 h, and the solvent was evaporated under high vacuum. The residue was partitioned between 200 mL of ether and 50 mL of aqueous 1 N sodium hydroxide solution, and the separated organic layer was washed with aqueous 1 N sodium hydroxide solution (1×50 mL), brine (1×100 mL), dried (Na2SO4), and evaporated to 1.16 g of a white solid. Recrystallization from hexane gave 1.06 g (85% yield) of the title compound as a white solid, mp 82-83° C. Anal. Calcd for C20H16FNO2: C, 74.75; H, 5.02; N, 4.36. Found: C, 74.63; H, 4.97; N, 4.31.

Workup

  1. customthe solvent was evaporated under high vacuum
  2. customThe residue was partitioned between 200 mL of ether and 50 mL of aqueous 1 N sodium hydroxide solution
  3. washthe separated organic layer was washed with aqueous 1 N sodium hydroxide solution (1×50 mL), brine (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to 1.16 g of a white solid
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-eb6e0249b1214c65bd0719d6eed60368
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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