Ammonium Chloride → 1-(4-Ethyl-4-penten-1-yl)-2-iodobenzene

HRID 600745ノート

反応式

HRID 600745 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[I:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15]C(=O)CC.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:2]([C:3](=[CH2:4])[CH2:15][CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[I:6])[CH3:1]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 116236086-(2-Iodophenyl)-3-hexanone2 回HCID 178418339Butyllithium

生成物 1

HCID 116379981-(4-Ethyl-4-penten-1-yl)-2-iodobenzene収率 60%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of methyltriphenylphosphonium bromide (21.76 g, 61 mmol) in dry ether (300 ml) was stirred at 0° C. under nitrogen. To this was added a 1.6M solution of butyl lithium (33.3 ml, 53.3 mmole) dropwise. Stirring at 0° C. was continued for 45 min then a solution of 6-(2-iodophenyl)-3-hexanone (Intermediate 10) (11.5 g, 38 mmol) in dry ether (40 ml) was added dropwise. Stirring at 0° C. was continued for 3 hours after which time aqueous ammonium chloride solution was added and the mixture was extracted with ether. The combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was slurried with cyclohexane to extract the crude product. Purification by SPE eluting with cyclohexane gave the title compound as a colourless liquid (6.8 g, 60%).

後処理

  1. stirringStirring at 0° C.
  2. stirringStirring at 0° C.
  3. waitwas continued for 3 hours
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. extractionto extract the crude product
  9. customPurification by SPE
  10. washeluting with cyclohexane

出典と根拠

ORDレコード
ord-0a4dcf269c9847688354bf6dea376217
出典データセット
uspto-grants-2011_03
特許番号
US07902224B2

反応ノート

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