Reaction #56483

Reaction equation

Sodium hydroxide

ethyl 4-{3-[3-(hydroxyoctyl)-4-oxo-2-thiazolidinyl]propyl}benzoate

chloroform

→

desired title compound

4-{3-[3-(3-Hydroxyoctyl)-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

NaCl

Solvents

methanol

water

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   Extractionextracted with ether
3. 3
   OtherThe aqueous phase is separated
4. 4
   Extractionextracted with ether
5. 5
   ExtractionThis ethereal extract
6. 6
   Washis washed with water
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Otherto yield an oil residue
10. 10
    WashElution with chloroform-acetic acid (25:1; v:v; 410 ml.)
11. 11
    Othergives impure material
12. 12
    Washelution with the same eluant (420 ml.)

Procedure

Sodium hydroxide solution (5 N, 2.5 ml., 12.5 mmol.) is added dropwise to a stirred mixture of ethyl 4-{3-[3-(hydroxyoctyl)-4-oxo-2-thiazolidinyl]propyl}benzoate (2.80 g., 6.64 mmol.) in aqueous methanol (25 ml. methanol plus 5 ml. water) maintained at 0° C. The resulting mixture is allowed to warm to room temperature and stirred for 3 hours. Then, the reaction mixture is diluted with water, and extracted with ether. The aqueous phase is separated, acidified with 2 N hydrochloric acid (10 ml.), and extracted with ether. This ethereal extract is washed with water, dried over anhydrous magnesium sulfate, concentrated in vacuo to yield an oil residue. The oil residue is then applied to a silica gel column (75 g.) with chloroform. Elution with chloroform-acetic acid (25:1; v:v; 410 ml.) gives impure material. Continued elution with the same eluant (420 ml.) provides the desired title compound as a viscous pale yellow oil, ir (NaCl) 1700, 1665 cm- 1, pmr (CDCl3) δ0.92 (3H, t), 3.60 (2H, s), 4.72 (1H, m), 7.30 (2H, d), 8.08 (2H, d).

Source