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

HRID 646786

Reaktionsgleichung

Reaktionsgleichung von HRID 646786
[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-c51ab133cae841cab65c35e212b069cf
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705177B2

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