Tetrabutylammonium Fluoride → Methyl 5-ethynylnicotinate

HRID 55305Notes

Reaction equation

HRID 55305 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:7]=[N:6][CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53821751Methyl 5-((trimethylsilyl)ethynyl)nicotinate

Product 1

HCID 53898384Methyl 5-ethynylnicotinateYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under the conditions of example 21 C, 464 mg of 5-(2-trimethylsilylethinyl)-nicotinic acid methyl ester is reacted with 2 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran, worked up, and the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate. 196 mg of 5-ethinylnicotinic acid methyl ester is obtained as oily crude product.

Workup

  1. customthe residue is chromatographed on silica gel with hexane/0-7% ethyl acetate

Sources & evidence

ORD record
ord-89d4abab64bb4dceb596cd3f470fa680
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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