Tetrabutylammonium Fluoride → 4-Ethynyl-benzeneacetic acid methyl ester

HRID 55297Notes

Reaction equation

HRID 55297 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[CH:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54516793Methyl 2-(4-(2-(trimethylsilyl)ethynyl)phenyl)acetate

Product 1

HCID 539703584-Ethynyl-benzeneacetic acid methyl esterYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 10 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester in 950 ml of tetrahydrofuran is mixed at 0° C. with 45 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran. The reaction mixture is stirred for 15 minutes at 0° C. and for 2 hours at room temperature and then concentrated by evaporation. The residue is spread between water and ethyl acetate, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate. 5.6 g of 4-ethinylphenylacetic acid methyl ester is obtained as oily crude product.

Workup

  1. concentrationconcentrated by evaporation
  2. customthe organic phase is dried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with hexane/0-7% ethyl acetate

Sources & evidence

ORD record
ord-09e6834678d94284b7b9a59bc53bfcd3
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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