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

HRID 2100487Notes

Reaction equation

HRID 2100487 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1.I[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:12][CH2:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:13])([F:14])[F:1])[CH:5]=1)[CH3:21]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 685102,6-Di-tert-butylpyridineHCID 106320752-(3-(Trifluoromethoxy)phenyl)ethanol

Product 1

HCID 68569118[2-(3-Trifluoromethoxy-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-trifluoromethoxy-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(3-trifluoromethoxy-phenyl)-ethoxy]-acetic acid ethyl ester as colorless oil. MS: m/e=293.1 [M+H+].

Sources & evidence

ORD record
ord-e2c22870fd22443a9dc1c4ba3e99ebe3
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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