Imidazole → Trimethyl[(2-methyl-1-phenoxybut-3-yn-2-yl)oxy]silane

HRID 26270

Reaction equation

HRID 26270 reaction equation
[OH:1][C:2]([CH3:13])([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[CH:4].N1C=CN=C1.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21].CCOCC.O>CN(C)C=O>[CH3:13][C:2]([O:1][Si:20]([CH3:22])([CH3:21])[CH3:19])([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[CH:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 21584184Diethylether waterHCID 232664582-Methyl-1-phenoxybut-3-yn-2-ol2×

Product 1

HCID 21325376Trimethyl[(2-methyl-1-phenoxybut-3-yn-2-yl)oxy]silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The hydroxyl group of this alkyne is protected by dissolving 2 parts of the butyne in 5 parts by volume of dimethylformamide and successively treating the reaction mixture with 2 parts of imidazole and 1.2 parts of trimethylsilylchloride. The reaction mixture is stirred at room temperature for 1 hour and poured into ether/water. The ethereal layer is washed with water and dried over anhydrous sodium sulfate. Isolation by low pressure liquid chromatography on silica gel provides 3-methyl-3-trimethylsilyloxy-4-phenoxy-1-butyne.

Workup

  1. washThe ethereal layer is washed with water
  2. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2d05f06d6e454e9bb29f86245611036f
Source dataset
uspto-grants-1979_04
Patent number
US04149006

Linked notes

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