Diisopropylethylamine → 4-(2-Triisopropylsilanyloxy-ethyl)-cyclohexanone

HRID 2422797

Reaktionsgleichung

Reaktionsgleichung von HRID 2422797
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(O[Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])(=O)=O>C(Cl)Cl>[CH:27]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[O:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 157003924-(2-Hydroxyethyl)cyclohexan-1-one

Produkt 1

HCID 219860994-(2-Triisopropylsilanyloxy-ethyl)-cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(2-hydroxy-ethyl)-cyclohexanone (Intermediate R10, 6.8 g, 52.6 mmol, (obtainable as described in the publication by Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016) was dissolved in CH2Cl2 (75 mL) and treated with diisopropylethylamine (9.2 mL, 52.6 mmol) followed by tri-isopropylsilyl trifluoromethane sulfonate (TIPSTf) (15.3 g, 50.2 mmol) at −30 EC. The reaction mixture was warmed to 0 EC for 1 h. The mixture was subjected to an aqueous work-up and purified by chromatography on SiO2 to give 4-(2-triisopropylsilanyloxy-ethyl)-cyclohexanone (Intermediate R11, 11.8 g (82%). Intermediate R11 was converted via Intermediate R12 to the unsaturated aldehyde, 5-(2-triisopropylsilanyloxy-ethyl)-cyclohex-1-enecarbaldehyde (Intermediate R13)

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to 0 EC for 1 h
  2. custompurified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-afe455de6a624d53ad69cf55ba35721d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960423B2

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