Potassium Carbonate → (4-Ethynyl-2-methyl-phenyl)-methanol

HRID 51797Notes

Reaction equation

HRID 51797 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:5]=[CH:4][C:3]=1[CH2:14][O:15][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([CH2:14][OH:15])=[C:2]([CH3:1])[CH:7]=1)#[CH:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 225688632-Methyl-4-trimethylsilanylethynyl-1-trimethlsilanyloxymethyl-benzene

Product 1

HCID 22568989(4-Ethynyl-2-methyl-phenyl)-methanolYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure E; 2-methyl-4-trimethylsilanylethynyl-1-trimethylsilananyloxymethyl-benzene (Intermediate 135, 380.0 mg, 1.30 mmols) in methanol (10 mL) was treated with potassium carbonate (180.0 mg, 1.3 mmol) and stirred overnight at ambient temperature. The crude alkyne was purified by column chromatography (5-20% EtOAc-hexanes) to give 100.0 mg (34%) of the title compound.

Workup

  1. customThe crude alkyne was purified by column chromatography (5-20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-7d611133bc2e4954929a037b94bc35a9
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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