Water → HCID 58372788, compound

HRID 656786Notes

Reaction equation

HRID 656786 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=2[CH2:27][S:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.O>C1COCC1>[CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=2[CH2:27][S:28][CH2:29][C:30]([F:33])([F:31])[F:32])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 58372836HCID 58372836, compound

Product 1

HCID 58372788HCID 58372788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-trimethylsilanylethynyl-phenyl}-acetic acid methyl ester (0.410 g, 0.8 mmol) in THF (3 mL) was added tetrabutylammonium fluoride (1M in THF; 1.2 mL, 1.2 mmol), and the reaction was stirred for 30 minutes at room temperature. Once no starting material was seen by analytical tlc, the mixture was worked-up with EtOAc and H2O, and the residue was purified by silica gel chromatography to give {4-Ethynyl-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester.

Workup

  1. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0cb67129e6d34bc9985e1a380d2d0b74
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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