HCID 11065736, compound → HCID 10857409, compound

HRID 1857535Notes

Reaction equation

HRID 1857535 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:7][CH:6]=1)(C)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 11065736HCID 11065736, compound

Product 1

HCID 10857409HCID 10857409, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[3-(4-isopropoxyphenyl)propyl]-2,4-oxazolidinedione (1.5 g) in dichloromethane (70 ml) was added dropwise titanium tetrachloride (TiCl4) (4.1 g) at 0° C. The mixture was stirred for one hour at the same temperature. The reaction mixture was poured into ice-water, and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate (MgSO4). The solvent was distilled off, and the residue was subjected to silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:4, v/v), 5-[3-(4-hydroxyphenyl)propyl]-2,4-oxazolidinedione (0.755 g, 59%) was obtained. Recrystallization from acetone-hexane gave colorless prisms. Melting point: 132-133° C.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. distillationThe solvent was distilled off
  5. washFrom the fractions eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-4322f3d254d94564b02c6ada4eca3436
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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