Methyl iodide → HCID 90111330, compound

Reaction equation

[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][CH:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].CI>C1COCC1>[CH3:9][C:10]([CH3:2])([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Procedure

To a solution of LDA (2.9 mL of 2 M) in THF (30 mL) at −78° C. add ethyl 2-methyl-3-[4-(trifluoromethyl)phenyl]propanoate (1 g, 3.85 mmol). Stir for 10 min, then add methyl iodide (1.48 g, 10.4 mmol) and stir for an additional 15 min Quench the reaction with 10 mL of 1 N HCl and allow to warm to ambient temperature. Extract with EtOAc (50 mL). Wash extract with brine, dry over sodium sulfate, filter, and concentrate. Purify the residue by flash chromatography (5% EtOAc in petroleum ether) to give the title compound (475 mg).