Imidazole → HCID 54757657, compound

HRID 41140Notes

Reaction equation

HRID 41140 reaction equation
[CH:1]([Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=1)([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:46]I>C(OCC)C.C(#N)C>[I:46][CH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][CH2:6][O:5][Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:1]([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 54757656(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)methanol

Product 1

HCID 54757657HCID 54757657, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 15 (0.500 g, 1.63 mmol), triphenylphosphine (1.280 g, 4.89 mmol), imidazole (0.360 g, 5.22 mmol) and iodine (1.320 g, 5.22 mmol) in diethyl ether (20 mL) and acetonitrile (6.0 mL) was stirred at 0° C. for 2 h. The reaction mixture was diluted with ether, and the resulting mixture was washed with water and a 20 wt % solution of thiosulfate in water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using ethyl acetate-hexanes 1:9 as eluent to provide the desired compound as colorless oil. Yield: 64%.

Workup

  1. washthe resulting mixture was washed with water
  2. dry with materiala 20 wt % solution of thiosulfate in water, dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-105d9e4fff2c49988f83e14a3ea3a662
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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