Trimethylacetamide → 2-tert-Butyl-4-(4-fluorophenyl)oxazole

HRID 729997

Reaction equation

HRID 729997 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14]([NH2:16])=[O:15]>O1CCOCC1>[C:13]([C:14]1[O:15][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:16]=1)([CH3:18])([CH3:17])[CH3:12]

Participants

4

Reactant 2

HCID 12957TrimethylacetamideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 668690432-tert-Butyl-4-(4-fluorophenyl)oxazoleYield 1,254.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reflux a solution of commercially available 2-bromo-4′-fluoroacetophenone (100.00 g, 460 mmol), 2,2-dimethyl-propionamide (93.06 g, 20 mmol) in 1,4-dioxane (600 mL) for 2 days. Filter precipitate, concentrate filtrate, and purify (silica gel chromatography, eluting with hexanes:EtOAc 60:1) to give the title compound (55 g, 55%).

Workup

  1. filtrationFilter precipitate
  2. concentrationconcentrate filtrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with hexanes:EtOAc 60:1)

Sources & evidence

ORD record
ord-52788692ddab4fcba992ec967028d476
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Linked notes

Loading…