TMS-Imidazole → (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one

HRID 1604835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604835
[OH:1][C:2]([CH3:23])([CH3:22])/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[CH2:7][C@H:8]([C@H:10]1[CH2:19][CH2:18][CH2:17][C@@H:16]2[C@:11]1([CH3:21])[CH2:12][CH2:13][CH2:14][C:15]2=[O:20])[CH3:9].[Si:24](C1NC=CN=1)([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[CH3:9][C@@H:8]([C@H:10]1[CH2:19][CH2:18][CH2:17][C@@H:16]2[C@:11]1([CH3:21])[CH2:12][CH2:13][CH2:14][C:15]2=[O:20])[CH2:7]/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[C:2]([CH3:22])([O:1][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH3:23]

Komponenten

4

Edukt 2

HCID 14420972TMS-ImidazoleHCID 86754888(4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-octahydro-naphthalen-1-one

Produkt 1

HCID 86754887(4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

323 mg of (4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-octahydro-naphthalen-1-one, was reacted at 40° with 1.33 ml of TMS-imidazole (9 equivalents) in 8 ml of CH2Cl2. After a few hours the mixture was poured onto crushed ice, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=9/1) yielded 326 mg of (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one as colourless oil.

Aufarbeitung

  1. additionAfter a few hours the mixture was poured
  2. customonto crushed ice
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a4756f5bf9f944ceb0f4c7886654674e
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994569

Notizen zur Reaktion

Wird geladen…