Sodium Iodide → Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate

HRID 468022

Reaktionsgleichung

Reaktionsgleichung von HRID 468022
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][CH2:7]1.[Na+].[I-:16]>CC(=O)CC.CCOCC>[I:16][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][CH2:7]1

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 21932003Ethyl 1-(4-chlorobutyl)-1-cyclobutanecarboxylate

Produkt 1

HCID 21932017Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-(4-chlorobutyl)-1-cyclobutanecarboxylate (21.21 g, 97.0 mmol) in 2-butanone (125 mL) was added NaI (19.07 g, 127 mmol). The reaction mixture was stirred under reflux for 20 h and diluted with Et2O (500 mL). The resulting mixture was washed with aqueous Na2S2O3 (10% (%), 250 mL), brine (250 mL), dried (Na2SO4) and evaporated in vacuo to give ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate (29.91 g, 99%) as a slightly yellow oil. 1H NMR (CDCl3): δ=4.14 (q, J=7.1 Hz, 2H), 3.17 (t, J=6.9 Hz, 2H), 2.49-2.32 (m, 2H), 1.98-1.69 (m, 8H), 1.37-1.19 (m, 2H), 1.27 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3): δ=176.5, 60.3, 47.5, 36.9, 33.7, 30.1 (2×), 26.0, 15.7, 14.5, 6.8. HRMS calcd for C11H20IO2 (MH+): 311.0508. found: 311.0511.

Aufarbeitung

  1. temperatureunder reflux for 20 h
  2. washThe resulting mixture was washed with aqueous Na2S2O3 (10% (%), 250 mL), brine (250 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bb4f80eea30b4cc9bce60db760812a1f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623915B2

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