Reaction #42775

Reaction equation

3-(4-Chlorophenyl)-7-hydroxy-8-iodo-2-isopropyl-chromen-4-one

1,3-bis(diphenylphosphino)propane

potassium carbonate

butyl vinyl ether

→

8-Acetyl-3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one

Solvents

N-methyl-2-pyrrolidinone

water

Water

Conditions

Workup

1. 1
   Otherthe tube is sealed
2. 2
   TemperatureThe mixture is cooled to room temperature
3. 3
   Extractionextracted with ethyl acetate (3×50 ml)
4. 4
   Washwashed with saturated brine (50 ml)
5. 5
   Dryingdried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   Otherto give a brown solid
9. 9
   OtherThis is purified by chromatography on silica gel
10. 10
    Otherto give a colourless solid

Procedure

3-(4-Chlorophenyl)-7-hydroxy-8-iodo-2-isopropyl-chromen-4-one (1.1 g, 2.5 mmol), 1,3-bis(diphenylphosphino)propane (206 mg, 0.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium carbonate (380 mg, 2.75 mmol) are mixed in N-methyl-2-pyrrolidinone (10 ml) in a 20 ml capacity microwave tube. Water (2 ml) and butyl vinyl ether (1.62 ml, 12.5 mmol) are added, the tube is sealed, and the mixture is heated at 80° C. under microwave irradiation for 45 min. The mixture is cooled to room temperature, poured into water (30 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated to give a brown solid. This is purified by chromatography on silica gel using cyclohexane/ethyl acetate (6:1) as eluant to give a colourless solid.

Source