반응 #93914

반응 방정식

sodium hydride

dimethyl-2-methylsulfonylazelate

1-iodo-4-acetoxynonane

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title compound

수율 129.3%

8-methylsulfonyl-12-hydroxyheptadecanoic acid

수율 129.3%

용매

dimethylformamide

반응 조건

후처리

1. 1
   세척is washed by decantation with petroleum ether
2. 2
   기타to remove the mineral oil
3. 3
   workup.ADDITIONadded dropwise at ambient temperature under a nitrogen atmosphere
4. 4
   온도cooled to ~10° C.
5. 5
   workup.ADDITIONadded at such a rate as
6. 6
   온도to maintain an internal temperature less than 35° C
7. 7
   workup.WAITAfter 19 hours at ambient temperature
8. 8
   여과the reaction mixture is filtered
9. 9
   세척Collected sodium iodide (17.1 g.) is washed with ether
10. 10
    농축The combined filtrate and washings are concentrated in vacuo at ~100° C.
11. 11
    기타yielding a residual oil which
12. 12
    기타is partitioned between ether and dilute hydrochloric acid
13. 13
    추출The organic extract
14. 14
    세척is washed with water and saturated brine
15. 15
    건조dried over magnesium sulfate
16. 16
    기타evaporated in vacuo

실험 절차

A suspension of 57% sodium hydride/mineral oil (3.84 g., 0.091 mole) is washed by decantation with petroleum ether to remove the mineral oil. The residual solid is suspended in dry dimethylformamide (100 ml.) and treated with a solution of dimethyl-2-methylsulfonylazelate (23.5 g., 0.08 mole) in dry dimethylformamide (60 ml.) added dropwise at ambient temperature under a nitrogen atmosphere. The resulting solution is stirred for 1 hour at room temperature, cooled to ~10° C., and treated with 1-iodo-4-acetoxynonane (30 g., 0.096 mole) added at such a rate as to maintain an internal temperature less than 35° C. After 19 hours at ambient temperature, the reaction mixture is filtered. Collected sodium iodide (17.1 g.) is washed with ether. The combined filtrate and washings are concentrated in vacuo at ~100° C. yielding a residual oil which is partitioned between ether and dilute hydrochloric acid. The organic extract is washed with water and saturated brine, dried over magnesium sulfate and evaporated in vacuo leaving the title compound as a viscous oil (37.7 g., 98%), pmr (CDCl3) δ 2.0 (s, 3H), 3.0 (s, 3H), 3.65 (s, 3H), 3.81 (s, 3H) and 4.9 (b, H).

출처