Triethylamine → Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide

HRID 978651Notes

Reaction equation

HRID 978651 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=2)[C:4](=[O:5])[O:3]1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CS(C)=O>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18](/[CH:19]=[CH:20]/[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[C:4](=[O:5])[O:3][CH:2]3[OH:1])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 80271Tri-o-tolylphosphineHCID 142348425-bromo-3-hydroxy-3H-isobenzofuran-1-one

Product 1

HCID 13827310Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 9.9 gm 3-hydroxy-5-bromophthalide, 5.8 gm p-methoxystyrene, 0.09 gm palladium acetate, 0.47 gm tri-(o-tolyl)-phosphine, 7 ml triethylamine and 35 ml dimethylsulfoxide were heated with stirring at 95° for 5 hours. The reaction mixture was cooled and added to 400 ml water. The product was extracted into ethyl acetate, which solution was washed with water and dried over magnesium sulfate. Removal of solvent left 8.0 gm yellow solid melting at 140°-148°.

Workup

  1. temperaturewere heated
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted into ethyl acetate, which solution
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent
  7. waitleft 8.0 gm yellow solid melting at 140°-148°

Sources & evidence

ORD record
ord-dad1e319ca0b42ce852803f8944d4b4f
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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