Imidazole → 1-Iodo-3,7-dimethyloctane

HRID 1819546Notes

Reaction equation

HRID 1819546 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4]O.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I>C1(C)C=CC=CC=1.CCCCCC>[I:36][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 77923,7-Dimethyl-1-octanolHCID 11776Triphenylphosphine

Product 1

HCID 142039361-Iodo-3,7-dimethyloctaneYield 71%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a stirring solution of 43 (5 g, 32 mmol), imidazole (2.59 g, 38 mmol, 1.2 eq) and triphenylphosphine (9.11 g, 35 mmol, 1.1 eq) in toluene (100 ml) under nitrogen was added iodine (10.44 g, 41 mmol, 1.3 eq). The reaction mixture was stirred for 18 hours then filtered. The filtrate was washed with 5% sodium thiosulfate solution (3×100 ml) then dried (Na2SO4) and concentrated in vacuo to give a white solid. This solid was taken up in hexane (20 ml), cooled and filtered. The filtrate was then concentrated in vacuo to give 45 (6 g, 71%) as a colourless oil.

Workup

  1. filtrationthen filtered
  2. washThe filtrate was washed with 5% sodium thiosulfate solution (3×100 ml)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a white solid
  6. temperaturecooled
  7. filtrationfiltered
  8. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-51822cc4742c4c9a8438c6ae2828e3a7
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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