反応 #93914

反応方程式

sodium hydride

dimethyl-2-methylsulfonylazelate

1-iodo-4-acetoxynonane

→

title compound

収率 129.3%

8-methylsulfonyl-12-hydroxyheptadecanoic acid

収率 129.3%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   洗浄is washed by decantation with petroleum ether
2. 2
   その他to remove the mineral oil
3. 3
   workup.ADDITIONadded dropwise at ambient temperature under a nitrogen atmosphere
4. 4
   温度cooled to ~10° C.
5. 5
   workup.ADDITIONadded at such a rate as
6. 6
   温度to maintain an internal temperature less than 35° C
7. 7
   workup.WAITAfter 19 hours at ambient temperature
8. 8
   ろ過the reaction mixture is filtered
9. 9
   洗浄Collected sodium iodide (17.1 g.) is washed with ether
10. 10
    濃縮The combined filtrate and washings are concentrated in vacuo at ~100° C.
11. 11
    その他yielding a residual oil which
12. 12
    その他is partitioned between ether and dilute hydrochloric acid
13. 13
    抽出The organic extract
14. 14
    洗浄is washed with water and saturated brine
15. 15
    乾燥dried over magnesium sulfate
16. 16
    その他evaporated in vacuo

実験手順

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).

出典