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

HRID 600745노트

반응식

HRID 600745 반응식
[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]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 116236086-(2-Iodophenyl)-3-hexanone2회HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매2회

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0a4dcf269c9847688354bf6dea376217
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902224B2

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