Ethyl iodoacetate → HCID 68568603, compound

HRID 2100484Notes

Reaction equation

HRID 2100484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.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:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 685102,6-Di-tert-butylpyridineHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 68568603HCID 68568603, compound

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

In analogy to the procedure described in example 78.1, 2-(4-fluoro-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(4-fluoro-phenyl)-ethoxy]-acetic acid ethyl ester as colorless liquid. 1H NMR (CDCl3): 1.28 (t, J=7.2 Hz, 3H), 2.92 (t, J=7.0 Hz, 2H), 3.73 (t, J=7.0 Hz, 2H), 4.07 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 6.97 (m, 2H), 7.21 (m, 2H).

Sources & evidence

ORD record
ord-2b475dde709f4f7297cf9a121ba4b998
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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