반응 #64414

반응 방정식

NaOH

1,5-pentanediol

NaBH4

1-nonene

→

5-(2-nonyloxy)pentanol

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타The solution is decanted from the mercuric salts
2. 2
   농축concentrated
3. 3
   기타The residue is partitioned between ethyl acetate and water
4. 4
   세척the organic layer is washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under vacuum
8. 8
   기타to give a clear liquid
9. 9
   기타chromatographed, initially with a 19 to 1 ratio of hexane to ethyl acetate

실험 절차

To a mixture of 12.6 grams of mercuric acetate and 8.3 grams of 1,5-pentanediol in 100 ml of dimethylformamide is added 5.0 grams of 1-nonene. The mixture is stirred at room temperature for ten minutes and 40 ml of an aqueous NaOH solution (3 Molar) is added followed by 40 ml of an aqueous NaBH4 solution (0.5 Molar in 3 Molar NaOH). The solution is decanted from the mercuric salts and concentrated. The residue is partitioned between ethyl acetate and water and the organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum to give a clear liquid. This liquid is flash chromatographed, initially with a 19 to 1 ratio of hexane to ethyl acetate and, subsequently, with a 9 to 1 ratio, to give 5-(2-nonyloxy)pentanol as a clear liquid.

출처