تفاعل #1049544

معادلة التفاعل

ethyl acetate

Racemic 1-O-octadecyl-2-O-benzyl-3-bromo-1,2-propanediol

tetrahydrofuran

sodium thiomethoxide

→

1-O-octadecyl-2-O-benzyl-3-methylthio-1,2-propanediol

المردود 90.0%

المذيبات

chloroform

hexane

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with a magnetic stir bar
2. 2
   ترشيحThe mixture was filtered
3. 3
   غسيلthe filtrate was washed with 50 ml tetrahydrofuran
4. 4
   تركيزThe combined filtrates were concentrated under vacuum
5. 5
   أخرىa rotary evaporator
6. 6
   أخرىto afford a yellow residue
7. 7
   غسيلthe organic solution washed twice with 30 ml of a concentrated solution of sodium bicarbonate
8. 8
   تجفيفThe organic phase was then dried over anhydrous magnesium sulfate
9. 9
   تركيزconcentrated on a rotary evaporator under vacuum
10. 10
    أخرىto afford the crude product as a pale yellow oily residue
11. 11
    أخرىThis crude product was purified by chromatography on silica gel 60 (E. Merck, Germany)
12. 12
    أخرىThe fractions collected
13. 13
    workup.ADDITIONThose fractions containing pure product (silica gel, 5% ethyl acetate in hexane, Rf=0.51)
14. 14
    تركيزconcentrated

الإجراء التجريبي

Racemic 1-O-octadecyl-2-O-benzyl-3-bromo-1,2-propanediol, 1.99 g (4.0 mmoles), was dissolved into 100 ml of dry tetrahydrofuran in a 250 ml round bottom flask equipped with a magnetic stir bar. To this solution was added 2.8 g (40.0 mmoles) of sodium thiomethoxide powder and the reaction mixture stirred for 4.5 hours at room temperature. The reaction was monitored by TLC (silica gel, 5% ethyl acetate in hexane; Rf=0.51). The mixture was filtered and the filtrate was washed with 50 ml tetrahydrofuran. The combined filtrates were concentrated under vacuum using a rotary evaporator to afford a yellow residue. This residue was dissolved into 50 ml chloroform and the organic solution washed twice with 30 ml of a concentrated solution of sodium bicarbonate. The organic phase was then dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator under vacuum to afford the crude product as a pale yellow oily residue. This crude product was purified by chromatography on silica gel 60 (E. Merck, Germany) using a step gradient of 0 to 10% ethyl acetate in hexane. The fractions collected were screened by TLC. Those fractions containing pure product (silica gel, 5% ethyl acetate in hexane, Rf=0.51) were pooled and concentrated to afford 1-O-octadecyl-2-O-benzyl-3-methylthio-1,2-propanediol in 90% yield.

المصدر