4-Methoxystyrene → HCID 54484814, compound

HRID 1584404Notes

Reaction equation

HRID 1584404 reaction equation
[CH2:1]([CH:8]([S:13]([C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[CH2:30])=[CH:27][CH:26]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([CH:8]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:30]=[CH:29][C:28]2[CH:31]=[CH:32][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 125074-MethoxystyreneHCID 80271Tri-o-tolylphosphineHCID 21224130HCID 21224130, compound

Product 1

HCID 54484814HCID 54484814, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-benzyl-3-(4-bromophenylsulfonyl)-propionic acid (250 mg), p-methoxystyrene (0.1 ml), diisopropylethylemine (0.25 ml), palladium acetate (5 mg) and tri(o-methylphenyl)phosphine (16 mg) was stirred overnight at 80° C. The reaction mixture was dissolved in methylene chloride and washed with aqueous citric acid. Solvent was removed from the methylene chloride solution, and the residue chromatographed on silica gel (preparative TLC, eluting with 10% methanol/methylene chloride), to afford 3-benzyl-3-(4-styrylphenylsulfonyl)-propionic acid (21 mg).

Workup

  1. washwashed with aqueous citric acid
  2. customSolvent was removed from the methylene chloride solution
  3. customthe residue chromatographed on silica gel (preparative TLC, eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-799301e504c545218cdc3df4da5e63b1
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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