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

HRID 468015

Reaktionsgleichung

Reaktionsgleichung von HRID 468015
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-172d914a6c9241059ab7d1003aa672e9
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623915B2

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