Iodoethane → Ethyl 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzoate

HRID 1657135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657135
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.C(=O)([O-])[O-].[K+].[K+].I[CH2:33][CH3:34]>CC(=O)CC>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:22][CH2:33][CH3:34])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 10314719Agn-190205

Produkt 1

HCID 13604828Ethyl 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

3.0 g (9 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzoic acid, 4 g (30 millimoles) of potassium carbonate and 2 9 g (18.9 millimoles) of iodoethane in 27 ml of butan-2-one were refluxed until conversion was complete (monitored by thin layer chromatography). When the mixture had cooled, the solid was filtered off, the filtrate was evaporated down and the residue was recrystallized from methanol to give 2.1 g (65%) of the title compound of melting point 137°-138° C.

Aufarbeitung

  1. temperatureWhen the mixture had cooled
  2. filtrationthe solid was filtered off
  3. customthe filtrate was evaporated down
  4. customthe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-9fc4dfa5e0424d42b2918d4004bf5344
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256694

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