Sodium Iodide → t-Butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylate

HRID 563159

反応式

HRID 563159 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[Na+].[I-:17]>CC(=O)CC.CCOCC>[I:17][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1

参加物

5

反応物 2

HCID 5238Sodium IodideHCID 21932032t-Butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate

生成物 1

HCID 21932054t-Butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylate収率 99.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a solution of tert-butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate (10.6 g, 45.7 mmol) in 2-butanone (50 mL) was added NaI (8.23 g, 54.5 mmol). The reaction mixture was stirred under reflux overnight, diluted with Et2O (100 mL), washed with a mixture of H2O (100 mL) and aqueous Na2S2O4 (0.5 M, 10 mL) and brine (50 mL). The organic phase was dried (Na2SO4) and evaporate in vacuo to give tert-butyl 1-(4-iodobutyl)-1-cyclopropanecarboxylate (14.8 g, 94% pure by GC, 94%) as a slightly yellow liquid. 1H NMR (CDCl3): δ=3.18 (t, J=6.9 Hz, 2H), 1.76 (quintet, J=7.1 Hz, 2H), 1.62-1.45 (m, 4H), 1.43 (s, 9H), 1.12 (dd, J=6.7 Hz, 3.8 Hz, 2H), 0.60 (dd, J=6.6 Hz, 3.9 Hz, 2H). 13C NMR (CDCl3): δ=173.9, 80.0, 33.8, 33.3, 28.9, 28.2 (3×), 24.2, 15.5 (2×), 7.2. HRMS calcd for C12H21IO2 (M+): 324.0587, found: 324.0587.

後処理

  1. temperatureunder reflux overnight
  2. washwashed with a mixture of H2O (100 mL) and aqueous Na2S2O4 (0.5 M, 10 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporate in vacuo

出典と根拠

ORDレコード
ord-4022edb1437c4c249be94e2618e1651c
出典データセット
uspto-grants-2011_11
特許番号
US08067466B2

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