Methyl iodide → (3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-trimethyl-silane

HRID 381169Notes

Reaction equation

HRID 381169 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]=1[OH:21])([CH3:4])([CH3:3])[CH3:2].[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si:13]([CH3:15])([CH3:16])[CH3:14])[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]=1[O:21][CH3:22])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 225689242,6-Di-tert-butyl4-trimethylsilanylethynyl-phenol2×

Product 1

HCID 22568920(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-trimethyl-silaneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution 2,6-di-tert-butyl-4-trimethylsilanylethynyl-phenol (Intermediate 167, 0.302 g, 1 mmol) in acetone (5 mL) was treated with potassium carbonate (0.138 g, 1 mmol) and methyl iodide (0.142 g, 1 mmol) and stirred overnight at room temperature. The volatiles were distilled off in vacuo and the residue was purified by flash column chromatography on silica gel (230-400 mesh) using ethyl acetate as the eluent to afford the title compound as a white solid (0.28 g, 90%).

Workup

  1. distillationThe volatiles were distilled off in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-5f5a2d68ad92499199760db44cdd9f7d
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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