Methyl iodide → HCID 54140284, compound

HRID 259877Notes

Reaction equation

HRID 259877 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[F:13].[H-].[Na+].I[CH3:17].[Cl-].[NH4+]>O1CCCC1.O>[CH3:17][O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:10])([CH3:12])[CH3:11])=[CH:5][C:4]=1[F:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22404147HCID 22404147, compound

Product 1

HCID 54140284HCID 54140284, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.98 g (10 mmol) of 2-hydroxymethyl-5-trimethylsilyl-1-fluorobenzene in 10 ml of tetrahydrofuran is added dropwise on a mixture of 0.24 g (10 mmol) of sodium hydride in 10 ml of tetrahydrofuran at 0° C. The reaction mixture is stirred 3 hours at room temperature and cooled to 0° C. A solution of 1.42 g (10 mmol) of iodomethane in 10 ml of tetrahydrofuran is added dropwise and the reaction mixture is stirred 15 hours at room temperature. A solution of 1.60 g (30 mmol) of ammonium chloride in 10 ml of water is added, the organic layer is separated, washed with brine, dried over MgSO4 and concentrated. The title compound is purified by distillation.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture is stirred 15 hours at room temperature
  3. customthe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. distillationThe title compound is purified by distillation

Sources & evidence

ORD record
ord-c08b616c1a7b410ebf1b47cafec8d906
Source dataset
uspto-grants-1996_06
Patent number
US05523442

Reaction notes

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