Ethyl iodoacetate → [2-(3-Trifluoromethyl-phenyl)-ethoxy]-acetic acid ethyl ester

HRID 2100513Notes

Reaction equation

HRID 2100513 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.I[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1)[CH3:20]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 685102,6-Di-tert-butylpyridineHCID 959263-(Trifluoromethyl)phenethylic alcohol

Product 1

HCID 68565644[2-(3-Trifluoromethyl-phenyl)-ethoxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

In analogy to the procedure described in example 78.1, 2-(3-trifluoromethyl-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(3-trifluoromethyl-phenyl)-ethoxy]-acetic acid ethyl ester as colorless liquid. MS: m/e=277.2 [M+H+].

Sources & evidence

ORD record
ord-d72ff45677254dbba9d0958366b8fe72
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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