Sodium Iodide → t-Butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylate

HRID 563159

Reaktionsgleichung

Reaktionsgleichung von HRID 563159
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[Na+].[I-:17]>CC(=O)CC.CCOCC>[I:17][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 21932032t-Butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate

Produkt 1

HCID 21932054t-Butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate (10.6 g, 45.7 mmol) in 2-butanone (50 mL) was added NaI (8.23 g, 54.5 mmol). The reaction mixture was stirred under reflux overnight, diluted with Et2O (100 mL), washed with a mixture of H2O (100 mL) and aqueous Na2S2O4 (0.5 M, 10 mL) and brine (50 mL). The organic phase was dried (Na2SO4) and evaporate in vacuo to give tert-butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylate (14.8 g, 94% pure by GC, 94%) as a slightly yellow liquid. 1H NMR (CDCl3): δ=3.18 (t, J=6.9 Hz, 2H), 1.76 (quintet, J=7.1 Hz, 2H), 1.62-1.45 (m, 4H), 1.43 (s, 9H), 1.12 (dd, J=6.7 Hz, 3.8 Hz, 2H), 0.60 (dd, J=6.6 Hz, 3.9 Hz, 2H). 13C NMR (CDCl3): δ=173.9, 80.0, 33.8, 33.3, 28.9, 28.2 (3×), 24.2, 15.5 (2×), 7.2. HRMS calcd for C12H21IO2 (M+): 324.0587, found: 324.0587.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. washwashed with a mixture of H2O (100 mL) and aqueous Na2S2O4 (0.5 M, 10 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4022edb1437c4c249be94e2618e1651c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067466B2

Verknüpfte Notizen

Wird geladen…