Ammonium Chloride → HCID 54211786, Verbindung

HRID 265350

Reaktionsgleichung

Reaktionsgleichung von HRID 265350
C([Li])CCC.[C:6]1([CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:17][O:18][C:19]1[CH2:26][CH2:25][C:22]2([O:24][CH2:23]2)[C:21](=[O:27])[CH:20]=1.[Cl-].[NH4+]>C(OCC)C.C1(C)C=CC=CC=1>[OH:27][C:21]1([CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:20]=[C:19]([O:18][CH3:17])[CH2:26][CH2:25][C:22]21[O:24][CH2:23]2

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 745735-Phenyl-1-pentyneHCID 190343736-Methoxy-1-oxaspiro[2.5]oct-5-en-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 54211786HCID 54211786, VerbindungAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

74 ml (0.118 mol) of n-butyllithium (1.6 molar in hexane) are added dropwise, under a nitrogen atmosphere, to a solution, cooled to -78° C., of 25 ml (0.157 mol) of 5-phenylpentyne in 400 ml of anhydrous diethyl ether. The whole is stirred at -78° C. for 15 minutes and then at 0° C. for 75 minutes. There is then added dropwise to that solution a solution, cooled to -78° C., of 6-methoxy-1-oxa-spiro[2.5]oct-5-en-4-one (11 g; 71.33 mmol) in 80 ml of anhydrous toluene. After 1 hour's stirring at -78° C., the reaction mixture is poured into an aqueous 10% ammonium chloride solution (1000 ml). Conventional treatment of the organic phase yields 22 g (74 mmol) of 4-hydroxy-6-methoxy-4-(5-phenylpenten-1-yl)-1-oxa-spiro[2.5]octene (2 isomers) in the form of an oily residue which is used in the following step without being purified. Hydrogenation of a solution of 22 g (74 mmol) of that mixture of isomers in 610 ml of benzene in the presence of 10 g of Lindlar catalyst for a period of 7 hours results, after filtration and evaporation, in 22 g (73 mmol) of 4-hydroxy-6methoxy-4-(5-phenylpentyl)-1-oxa-spiro[2.5]oct-5-ene in the form of an oily residue which is used in the following step without being purified.

Aufarbeitung

  1. waitat 0° C. for 75 minutes
  2. additionThere is then added dropwise to that solution a solution
  3. stirringAfter 1 hour's stirring at -78° C.

Quellen und Nachweise

ORD-Eintrag
ord-f305ffeb72e345eb8bc4620c15cd39fc
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648382

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