Acetone → (R)-6-Cyclohexyl-4-methyl-hexanal

HRID 132629

反応式

HRID 132629 の反応式
[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]2[O:14]C2(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=O.I([O-])(=O)(=O)=O.[K+]>O>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 180AcetoneHCID 516896Potassium periodateHCID 865979603-((R)-5-Cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane

生成物 1

HCID 86597961(R)-6-Cyclohexyl-4-methyl-hexanal収率 81.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A flask was charged with 10.65 g (44.7 mmol) of 3-((R)-5-cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane, 70 mL of acetone, 12.3 g (53.6 mmol) of potassium periodate, 70 mL of water, and 0.765 g (4 mmol) of tosic acid-monohydrate. The mixture was stirred for 46 hours. The acetone was removed under reduced pressure, and the mixture was diluted with water. The aqueous layer was extracted with hexanes and dried with sodium sulfate. The drying agent was filtered off and solvent was removed under reduced pressure to get 7.12 g (81% yield) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.87 (m, 5H) 1.13 (m, 3H) 1.25 (m, 5H) 1.66 (m, 8H) 2.40 (m, 2H) 9.75 (s, 1H). MS (APCI) m+1/z is inconclusive.

後処理

  1. customThe acetone was removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. extractionThe aqueous layer was extracted with hexanes
  4. dry with materialdried with sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customsolvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-6b8f5bed32b24deb870c583f9c4eceee
出典データセット
uspto-grants-2008_06
特許番号
US07388023B2

関連ノート

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