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

HRID 563166

반응식

HRID 563166 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 21932017Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate수율 99.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

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% (w/w), 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.

후처리

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

출처 및 근거

ORD 기록
ord-9a43771c41e644559864650a8e025b9a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067466B2

연결된 노트

불러오는 중…