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

HRID 349810

반응식

HRID 349810 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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, 5 H) 1.13 (m, 3 H) 1.25 (m, 5 H) 1.66 (m, 8 H) 2.40 (m, 2 H) 9.75 (s, 1 H). MS (APCl) m+1/z is inconclusive.

후처리

  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

출처 및 근거

ORD 기록
ord-384080e762e74e949192c3de0da165d2
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179934B2

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