Butyl vinyl ether → 8-Acetyl-3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one

HRID 14497

Reaction equation

HRID 14497 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12](I)[C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH:59]([O:61]CCCC)=[CH2:60]>CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:59]([C:12]1[C:13]([OH:19])=[CH:14][CH:15]=[C:16]2[C:11]=1[O:10][C:9]([CH:21]([CH3:23])[CH3:22])=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:17]2=[O:18])(=[O:61])[CH3:60]

Participants

8

Reactant 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 597242463-(4-Chlorophenyl)-7-hydroxy-8-iodo-2-isopropyl-chromen-4-one

Product 1

HCID 597242698-Acetyl-3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

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.

Workup

  1. customthe tube is sealed
  2. temperatureThe mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washwashed with saturated brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown solid
  9. customThis is purified by chromatography on silica gel
  10. customto give a colourless solid

Sources & evidence

ORD record
ord-1f7d75009f3e45e8b5f63eb1176a7c1f
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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