Water → HCID 11806663, compound

HRID 1739041Notes

Reaction equation

HRID 1739041 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:7][CH:6]=1)(C)C.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 11747919HCID 11747919, compound

Product 1

HCID 11806663HCID 11806663, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride (3.67 g) was added dropwise to a solution of 5-[2-(4-isopropoxyphenyl)ethyl]-2,4-thiazolidinedione (1.35 g) in dichloromethane (70 ml) at 0° C. After stirring for 2 hours, the mixture was poured into ice-cooled water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:3, v/v) gave 5-[2-(4-hydroxyphenyl)ethyl]-2,4-thiazolidinedione (0.72 g, 63%). This product was recrystallized from acetone-isopropyl ether. Colorless prisms, mp: 175-176° C.

Workup

  1. additionthe mixture was poured into ice-
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe fractions eluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-ca9132aaf65d484f85da08dee8ab29aa
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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