Diisopropylamine → 2-Fluoro-2-methyl-1-tetralone

HRID 1656808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656808
C(NC(C)C)(C)C.C([Li])CCC.C(NC(C)C)(C)C.[Li].[CH3:21][CH:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:43])(=O)=O)=CC=1>O1CCCC1>[CH3:21][C:22]1([F:43])[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32]

Komponenten

7

Edukt 5

HCID 7912DiisopropylamineHCID 1026502-Methyl-1-tetraloneHCID 588007N-FluorobenzenesulfonimideHCID 45051747Lithium diisopropylamineHCID 178418339Butyllithium

Produkt 1

HCID 150144562-Fluoro-2-methyl-1-tetraloneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

0.16 milliliter diisopropylamine in 10 milliliters tetrahydrofuran were allowed to stand with 1.15 equivalents butyllithium at -25° C. The resulting solution of lithium diisopropylamine was cooled to -78° C. and 1 equivalent 2-methyl-1-tetralone in 5 milliliters tetrahydrofuran solution was dropped in. The mixture was allowed to stand at -70° C. for 100 minutes. 1.5 equivalents N-fluorobenzenesulfonimide prepared according to Example 1 above in 11 milliliters tetrahydrofuran were mixed rapidly with the mixture at -95° C. The mixture was quenched with 30 milliliters ammonium chloride solution and extracted with dichloromethane. The organic phase was dried with magnesium sulfate, filtered, and evaporated. 2-methyl-2-fluoro-tetralone was obtained in 50% yield.

Aufarbeitung

  1. additionwere mixed rapidly with the mixture at -95° C
  2. customThe mixture was quenched with 30 milliliters ammonium chloride solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-225051308dab4752838f27b03d9e6062
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254732

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