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

HRID 841721Notes

Reaction equation

HRID 841721 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-aca82a092da949449ccb66aec65a0a85
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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