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

HRID 26776노트

반응식

HRID 26776 반응식
[OH:1][CH2:2][C@H:3]([CH3:16])[CH2:4][C:5](=O)[CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].[OH-].[K+].O.NN>C(O)COCCO>[CH3:16][C@H:3]([CH2:4][CH2:5][CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:2][OH:1]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11042498(2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one

생성물 1

HCID 10353213(2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

시약·촉매·용매 1

HCID 8117Diethylene Glycol용매

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).

후처리

  1. additionA mixture of 3.98 g
  2. temperatureheated until distillation
  3. distillationDistillation
  4. customreached 195° C.
  5. temperatureat reflux for 4 hours
  6. temperatureAfter cooling
  7. additionthe resulting mixture was treated with ice and 3 N aqueous HCl
  8. extractionworked-up by ether extraction in the manner of Example 1 giving 2.9 g
  9. customThis material was chromatographed on 180 g
  10. washElution with 4:1 parts by volume hexane-ether

출처 및 근거

ORD 기록
ord-3ebd2558f3104815a5ab360475dfe70b
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151205

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