Pyridine → 2-(4-Fluorophenylacetoxy)-4'-(methylthio)isobutyrophenone

HRID 964348Notes

Reaction equation

HRID 964348 reaction equation
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][CH:23]=1>C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=2)=[O:4])=[O:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37449884-Fluorophenylacetyl chlorideHCID 114131682-Hydroxy-4'(methylthio)isobutyrophenone

Product 1

HCID 206584842-(4-Fluorophenylacetoxy)-4'-(methylthio)isobutyrophenoneYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 72 mg (0.34 mmol) 2-hydroxy-4'-(methylthio)isobutyrophenone in 1.7 mL of CH2Cl2 were added 0.2 mL of pyridine and 140 mg (0.81 mmol) of 4-fluorophenylacetyl chloride. The mixture was stirred at room temperature overnight and then quenched with NH4OAc buffer. The product was extracted with EtOAc, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography eluting with 8:1 hexane/EtOAc to give 95 mg of the title product.

Workup

  1. customquenched with NH4OAc buffer
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting with 8:1 hexane/EtOAc

Sources & evidence

ORD record
ord-1fe5096d47e74bd2b069b0d43fdd3118
Source dataset
uspto-grants-1998_06
Patent number
US05767291

Reaction notes

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