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

HRID 2100526Notes

Reaction equation

HRID 2100526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].I[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:17]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 685102,6-Di-tert-butylpyridineHCID 88266o-Chlorophenethylic alcohol

Product 1

HCID 68567706[2-(2-Chloro-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-(2-chloro-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(2-chloro-phenyl)-ethoxy]-acetic acid ethyl ester as yellow liquid. 1H NMR (CDCl3): 1.28 (t, J=7.3 Hz, 3H), 3.09 (t, J=7.1 Hz, 2H), 3.78 (t, J=7.1 Hz, 2H), 4.09 (s, 2H), 4.21 (q, J=7.3 Hz, 2H), 7.13-7.23 (m, 2H), 7.29-7.37 (m, 2H).

Sources & evidence

ORD record
ord-d64ad3ea76274c5ebf6c4225a9a313b7
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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