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

HRID 1735453Notes

Reaction equation

HRID 1735453 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-31a4cd55cb1e4cfa91104e5ba655eac3
Source dataset
uspto-grants-1996_07
Patent number
US05536752

Reaction notes

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