Imidazole → (4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl-octahydro-naphtalen-1-one

HRID 1075558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075558
[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][C@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH3:7].[CH3:22][Si:23](C1NC=CN=1)([CH3:25])[CH3:24].C[Si](Cl)(C)C.N1C=CN=C1>O1CCCC1>[CH3:7][C@@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH2:5][CH2:4][CH2:3][C:2]([CH3:20])([O:1][Si:23]([CH3:25])([CH3:24])[CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 11022791(4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-oneHCID 14420972TMS-Imidazole

Produkt 1

HCID 70273562(4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl-octahydro-naphtalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 24 mg (0.08 mMol) of (4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-one in 0.5 ml of tetrahydrofuran is cooled under stirring and Argon atmosphere to 0°. The reaction mixture is stirred for an additional hour after addition of 12 μl (0.08 mMol) of trimethylsilylimidazole, of 5.1 μl (0.04 mMol) of trimethylsilylchloride and of 2.8 mg (0.04 mMol) of imidazole. The reaction mixture is poured into ice water, extracted three times with diethylether, the combined organic extracts are washed twice with brine and dried over Na2SO4. The organic solvent is evaporated in vacuo and the residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1 to yield 25 mg of pure, oily (4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl -octahydro-naphtalen-1-one

Aufarbeitung

  1. customto 0°
  2. stirringThe reaction mixture is stirred for an additional hour
  3. extractionextracted three times with diethylether
  4. washthe combined organic extracts are washed twice with brine
  5. dry with materialdried over Na2SO4
  6. customThe organic solvent is evaporated in vacuo
  7. customthe residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1

Quellen und Nachweise

ORD-Eintrag
ord-7e90d3077e4945459e8b3d1087ddc67b
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05905074

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