Water → (E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene

HRID 53493

반응식

HRID 53493 반응식
[CH:1]1[C:2]([I:10])=[CH:3][C:4]([I:9])=[C:5]([OH:8])[C:6]=1[I:7].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20].O>CN(C)C=O>[I:7][C:6]1[CH:1]=[C:2]([I:10])[CH:3]=[C:4]([I:9])[C:5]=1[O:8][CH2:17]/[CH:18]=[C:19](\[CH3:20])/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

생성물 1

HCID 15343331(E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A mixture of triiodophenol (10.0 g, 21.2 mmol), milled potassium carbonate (3.1 g, 22.5 mmol, 1.06 eq) and geranyl bromide (4.0 ml, 20.2 mmol) in dimethyl formamide (25 ml) was heated to 50° C. for 2 hrs and cooled. The mixture was poured into 300 ml of water and extracted with ethyl acetate. The ethyl acetate extract was filtered through a short pad of silica gel, then alumina, eluting with ethyl acetate-hexanes (1:1). The eluent was concentrated under high vacuum to give the product in 87% yield as an oil.

후처리

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. filtrationwas filtered through a short pad of silica gel
  5. washalumina, eluting with ethyl acetate-hexanes (1:1)
  6. concentrationThe eluent was concentrated under high vacuum
  7. customto give the product in 87% yield as an oil

출처 및 근거

ORD 기록
ord-e22a45abcb974474bdf8c81aa359d759
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620677

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