Toluene → HCID 54196646, compound

HRID 322960Notes

Reaction equation

HRID 322960 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8](=[O:23])[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH2:24]([S:31][Sn](C)(C)C)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:36]1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:24]([S:31][C:2]1[CH:3]=[C:4]([C:8](=[O:23])[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:36])=[O:13])[CH:5]=[CH:6][CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 22010525HCID 22010525, compoundHCID 54018710methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate

Product 1

HCID 54196646HCID 54196646, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate (1.7 g), bis(triphenylphosphine)palladium (II) chloride (0.1 g), tetrakis(triphenylphosphine)palladium (0) (0.13 g) and benzylthiotrimethylstannane (1.17 g) in toluene (37 mL) is heated at reflux for 24 hours. The reaction mixture is washed twice with 10% aqueous potassium fluoride (20 mL), with water (20 mL), dried over magnesium sulphate and evaporated. The residue (2.87 g) is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (98:2 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-5-(3-benzylthiophenyl)-4-(2-methylphenyl)-5-oxopentanoate as an orange oil (0.57 g).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. washThe reaction mixture is washed twice with 10% aqueous potassium fluoride (20 mL), with water (20 mL)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue (2.87 g) is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (98:2 v/v)
  7. customevaporated

Sources & evidence

ORD record
ord-48d4164fa31447b28fdce88dcf2a3769
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…