HCID 53811871, compound → HCID 67643022, compound

HRID 863106Notes

Reaction equation

HRID 863106 reaction equation
[C:1]([C:9](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]2[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:1](=[O:8])[CH:9]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 53811871HCID 53811871, compound

Product 1

HCID 67643022HCID 67643022, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 2-benzoyl-3-(4-hydroxyphenyl)propenoate (0.50 g, 1.7 mmol) in CH2Cl2 (15 ml) at 0° C. under an argon atmosphere was added titanium tetrachloride (0.93 ml, 8.3 mmol). The resulting mixture was allowed to stir at room temperature overnight. The reaction was slowly quenched with 3M HCl, then partitioned between EtOAc (50 ml) and 3M HCl. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with H2O and saturated aqueous NaCl, and dried (Na2SO4). The solvent was removed in vacuo, and the solid residue was recrystallized from EtOAc/hexanes to afford the title compound (410 mg, 82%).

Workup

  1. customThe reaction was slowly quenched with 3M HCl
  2. custompartitioned between EtOAc (50 ml) and 3M HCl
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic extracts were washed successively with H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe solid residue was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-ea00c1e98e344accb7e34c4a6e2fb7b7
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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