Trimethylsilyl iodide → HCID 15890171, compound

HRID 399046Notes

Reaction equation

HRID 399046 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([CH3:11])[CH3:10])=[CH:5][CH:4]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)([CH3:11])[CH3:10])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 12236299HCID 12236299, compound

Product 1

HCID 15890171HCID 15890171, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[1-(4-fluorophenyl)-1-methylethyl]phenyl methyl ether (3.34 g, 13.67 mmol) in chloroform (40 ml) was added trimethylsilyl iodide (4.10 g, 20.51 mmol). The solution was stirred under argon at 40° C. for 18 h, then cooled and poured into ice cold water (50 ml). The aqueous phase was extracted with chloroform (6×20 ml), and the combined organic layers were washed with sodium metabisulfite then brine, and dried over sodium sulfate. After concentration in vacuo the residue was subjected to column chromatography on silica gel eluting with 10-40% diethyl ether in 40-60 petroleum ether to afford the title compound as an oil (2.4 g).

Workup

  1. temperaturecooled
  2. extractionThe aqueous phase was extracted with chloroform (6×20 ml)
  3. washthe combined organic layers were washed with sodium metabisulfite
  4. dry with materialbrine, and dried over sodium sulfate
  5. concentrationAfter concentration in vacuo the residue

Sources & evidence

ORD record
ord-687f7d8534534c8fa5ee4e6ffc0cb728
Source dataset
uspto-grants-1998_10
Patent number
US05817698

Reaction notes

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