Potassium bisulfate → HCID 178486039, Verbindung

HRID 25640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25640
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+].OS([O-])(=O)=O.[K+]>CCOCC>[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:10][CH2:11][C@H:12](/[CH:15]=[CH:16]/[CH2:17][OH:18])[CH2:13][CH2:14]1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 516920Potassium bisulfateHCID 16684438Red-Al2×HCID 178486040HCID 178486040, Verbindung

Produkt 1

HCID 178486039HCID 178486039, VerbindungAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 4.5 g (16.8 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 180 ml Et2O was cooled (0° C.) and treated slowly with a solution of 13.46 ml (47.1 mmol) of Red-Al (70% in toluene). The solution was stirred 2 h at RT, cooled (0° C.) and treated again with 1.3 ml (4.7 mmol) of Red-Al (70% in toluene). After 2 h at RT, the reaction was cooled (−50° C.) and hydrolyzed with a suspension of 3 g MgSO4.7H2O, 3 g silicagel in 4 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was filtered. After evaporation, the residue was dissolved in CH2Cl2, dried over Na2SO4 and evaporated to yield 3.59 g (quantitative) of trans-(1E)-[4-(3-Hydroxy-propenyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 270 (MH+).

Aufarbeitung

  1. temperaturecooled (0° C.)
  2. waitAfter 2 h at RT
  3. temperaturethe reaction was cooled (−50° C.)
  4. customThe cooling bath was removed
  5. additionTHF was added
  6. filtrationthe mixture was filtered
  7. customAfter evaporation
  8. dissolutionthe residue was dissolved in CH2Cl2
  9. dry with materialdried over Na2SO4
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f06f50d402ee45feb65688214ec90e0a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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