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

HRID 646786

반응식

[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

참가 물질

반응물 3

HCID 813641-Bromo-4-chlorobutane

HCID 84700Ethyl cyclobutanecarboxylate

HCID 2724682Lithium diisopropylamide

생성물 1

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

반응 조건

온도: 0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-c51ab133cae841cab65c35e212b069cf
출처 데이터셋: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07705177B2

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