تفاعل #56482

معادلة التفاعل

mercaptoacetic acid

hydrochloric acid

Ethyl 4-(4-oxobutyl)benzoate

1-amino-3-(tetrahydro-2H-pyran-2-yloxy)octane

sodium sulfate

→

title compound

المردود 31.6%

Ethyl 4-{3-[3-(3-Hydroxyoctyl)-4-oxo-2-thiazolidinyl]propyl}benzoate

المردود 31.6%

المذيبات

water

chloroform

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred for 1 hour
2. 2
   أخرىThe solid is subsequently removed by filtration
3. 3
   غسيلwashed with a small quantity of benzene
4. 4
   workup.ADDITIONThe combined filtrate and washings are diluted with benzene (70 ml.)
5. 5
   درجة الحرارةThe resulting solution is refluxed in a Dean-Stark apparatus for 3 hours
6. 6
   غسيلwashed successively with dilute hydrochloric acid, 5% sodium bicarbonate
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   تركيزconcentrated
9. 9
   أخرىto give an oil residue
10. 10
    workup.STIRRINGstirred at ambient temperature for 16 hours
11. 11
    استخلاصfollowed by extraction with ether
12. 12
    استخلاصThe ethereal extract
13. 13
    غسيلis washed with water, 5% sodium bicarbonate
14. 14
    تجفيفdried over anhydrous magnesium sulfate
15. 15
    ترشيحfiltered
16. 16
    أخرىEvaporation of the filtrate in vacuo
17. 17
    أخرىprovides an oil residue which
18. 18
    غسيلElution with chloroform-methanol (100:1; v:v; 1950 ml.)
19. 19
    أخرىprovides impure material
20. 20
    غسيلfurther elution with the same eluant (450 ml.)

الإجراء التجريبي

Ethyl 4-(4-oxobutyl)benzoate (4.63 g., 21 mmol.) is added dropwise to 1-amino-3-(tetrahydro-2H-pyran-2-yloxy)octane (4.82 g., 21 mmol.) at ambient temperature. The resulting mixture is stirred for 15 minutes before adding anhydrous sodium sulfate (4 g.), and then stirred for 1 hour. The solid is subsequently removed by filtration and washed with a small quantity of benzene. The combined filtrate and washings are diluted with benzene (70 ml.) and then treated with mercaptoacetic acid (1.93 g., 21 mmol.). The resulting solution is refluxed in a Dean-Stark apparatus for 3 hours. The reaction mixture is allowed to cool to room temperature, washed successively with dilute hydrochloric acid, 5% sodium bicarbonate, dried over anhydrous magnesium sulfate, and concentrated to give an oil residue. A methanol solution (50 ml.) of the oil residue is treated with concentrated hydrochloric acid (0.2 ml.) and then stirred at ambient temperature for 16 hours. The reaction mixture is diluted with cold water, followed by extraction with ether. The ethereal extract is washed with water, 5% sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo provides an oil residue which is then applied to a silica gel column (300 g.) with chloroform. Elution with chloroform-methanol (100:1; v:v; 1950 ml.) provides impure material; further elution with the same eluant (450 ml.) gives the title compound as a pale yellow oil (2.80 g., 6.64 mmol., 31%), pmr (CDCl3) δ0.90 (3H, t), 1.40 (3H, t), 3.53 (2H, s), 4.40 (2H, q), 4.70 (1H, m), 7.22 (2H, d), 8.0 (2H, d).

المصدر