반응 #55054

반응 방정식

(2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one

KOH

hydrazine hydrate

→

(2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

용매

diethylene glycol

반응 조건

후처리

1. 1
   workup.ADDITIONA mixture of 3.98 g
2. 2
   온도heated until distillation
3. 3
   workup.DISTILLATIONDistillation
4. 4
   기타reached 195° C.
5. 5
   온도at reflux for 4 hours
6. 6
   온도After cooling
7. 7
   workup.ADDITIONthe resulting mixture was treated with ice and 3 N aqueous HCl
8. 8
   추출worked-up by ether extraction in the manner of Example 1 giving 2.9 g
9. 9
   기타This material was chromatographed on 180 g
10. 10
    세척Elution with 4:1 parts by volume hexane-ether

실험 절차

A mixture of 3.98 g. (0.0174 mole) of (2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one, 108 ml. of diethylene glycol, 25 g. of KOH and 43.5 ml. of hydrazine hydrate was stirred and heated until distillation began. Distillation was then continued until the internal temperature of the reaction mixture reached 195° C. then the mixture was mintained at reflux for 4 hours. After cooling, the resulting mixture was treated with ice and 3 N aqueous HCl and worked-up by ether extraction in the manner of Example 1 giving 2.9 g. of a pale yellow oil. This material was chromatographed on 180 g. of silica gel. Elution with 4:1 parts by volume hexane-ether yielded (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol which was evaporatively distilled affording 2.22 g. of a colorless oil, b.p. 90°-105° C. (bath temperature) (0.2 mm Hg.); [α]25D+ 9.44° (c 2.04, hexane).

출처