Tetrabutylammonium Fluoride → N-(3-ethynylphenyl)-1,1,1-trifluoromethanesulfonamide

HRID 55308Notes

Reaction equation

HRID 55308 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:4]([C:5]1[CH:6]=[C:7]([NH:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)#[CH:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19957475N-[3-(2-trimethylsilylethinyl)-phenyl]-1,1,1-trifluoromethanesulfonamide

Product 1

HCID 19957419N-(3-ethynylphenyl)-1,1,1-trifluoromethanesulfonamideYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under the conditions of example 21 C, 2 g of N-[3-(2-trimethylsilylethinyl)-phenyl]-1,1,1-trifluoromethanesulfonamide is reacted with 6.9 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran and worked up. 387 mg of N-(3-ethinylphenyl)-1,1,1-trifluoromethanesulfonamide is obtained as oily crude product.

Sources & evidence

ORD record
ord-c1ebe54cd5b54babae77f5eaa3a4f56b
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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