Phenyl Trifluoromethanesulfonate → 2-Triethylsilyl-5-phenyl-4-furaldehyde

HRID 273954

Reaction equation

HRID 273954 reaction equation
[CH2:1]([Si:3]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:4]1[O:5][CH:6]=[C:7]([CH:9]=[O:10])[CH:8]=1)[CH3:2].[Li]N(C)CCN(C)C.FC(F)(F)S(O[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=O)=O>[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([Si:3]([CH2:11][CH3:12])([CH2:1][CH3:2])[C:4]1[O:5][C:6]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:7]([CH:9]=[O:10])[CH:8]=1)[CH3:14]

Participants

6

Reactant 3

HCID 548641Phenyl TrifluoromethanesulfonateHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-HCID 178506926HCID 178506926, compound

Product 1

HCID 194331442-Triethylsilyl-5-phenyl-4-furaldehyde

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Treatment of 2-triethylsilyl-4-furaldehyde with lithio N,N,N'-trimethylethylenediamine, followed by phenyl trifluoromethanesulfonate in the presence of anhydrous zinc chloride and tetrakis (triphenylphosphine) palladium (O) provides the titled aldehyde.

Sources & evidence

ORD record
ord-26f409491456488d805acea1c1652e38
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Linked notes

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