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

HRID 2072340ノート

反応式

HRID 2072340 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8117Diethylene Glycol溶媒

実験手順

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 wan then continued until the internal temperature of the reaction mixture reached 195° C. then the mixture was maintained 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 l g. of a colorless oil, b.p. 90- 105° C. (bath temperature (0.2 mm Hg.); [α]25D + 9.44° (c 2.04, hexane).

後処理

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

出典と根拠

ORDレコード
ord-d2a5e47da46c40c682c6fbcd94d3fc7a
出典データセット
uspto-grants-1977_09
特許番号
US04051153

反応ノート

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