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

HRID 24231Notes

Reaction equation

HRID 24231 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-c328ca38ef2d47a995224e4967ad99f0
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

Loading…