تفاعل #56483

معادلة التفاعل

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

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature
2. 2
   استخلاصextracted with ether
3. 3
   أخرىThe aqueous phase is separated
4. 4
   استخلاصextracted with ether
5. 5
   استخلاصThis ethereal extract
6. 6
   غسيلis washed with water
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىto yield an oil residue
10. 10
    غسيلElution with chloroform-acetic acid (25:1; v:v; 410 ml.)
11. 11
    أخرىgives impure material
12. 12
    غسيلelution with the same eluant (420 ml.)

الإجراء التجريبي

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).

المصدر