1-Bromo-4-chlorobutane → Ethyl 1-(4-chlorobutyl)-1-cyclobutanecarboxylate

HRID 239040

Reaktionsgleichung

Reaktionsgleichung von HRID 239040
[Li+].CC([N-]C(C)C)C.[CH:9]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10]1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]>>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][C:9]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 3

HCID 813641-Bromo-4-chlorobutaneHCID 84700Ethyl cyclobutanecarboxylateHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 21932003Ethyl 1-(4-chlorobutyl)-1-cyclobutanecarboxylate

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound 104b was prepared, likewise the procedure described for 104c, starting from LDA (prepared from BuLi (2.5M in hexanes, 52.8 mL, 132 mmol) and iPr2NH (18.52 mL, 132 mmol, distilled from NaOH)), ethyl 1-cyclobutanecarboxylate (Török, B. et al. J. Chem. Soc. Perkin Trans. 1, 1993, 7, 801-804) (14.05 g, 110 mmol) (the resulting mixture was allowed to warm to 0° C. and cooled again to −60° C.) and 1-bromo-4-chlorobutane (19.1 mL, 165 mmol) to give, after purification by fractional distillation under reduced pressure, 104b (20.53 g, 86%) as a thin, colorless oil. bp: T=64-71° C. (p=0.001 Torr). 1H NMR: δ 4.13 (q, J=7.1 Hz, 2H), 3.51 (t, J=6.8 Hz, 2H), 2.50-2.32 (m, 2H), 1.96-1.70 (m, 8H), 1.40-1.20 (m, 2H), 1.26 (t, J=7.2 Hz, 3H). 13C NMR: δ 176.6, 60.3, 47.6, 44.8, 37.3, 32.8, 30.1 (2×), 22.4, 15.8, 14.4.

Aufarbeitung

  1. customto give
  2. customafter purification
  3. distillationby fractional distillation under reduced pressure, 104b (20.53 g, 86%) as a thin, colorless oil
  4. customT=64-71° C. (p=0.001 Torr)

Quellen und Nachweise

ORD-Eintrag
ord-0c56a872aa6940b892257625f0cb0f13
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642653B2

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