Methyl iodide → Methyl 2-[3-methoxy-5-(trifluoromethyl)phenyl]propanoate

HRID 1686423Notes

Reaction equation

HRID 1686423 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([O:15][CH3:16])[CH:6]=1.[CH2:18]([Li])CCC.C(NC(C)C)(C)C.IC>C1COCC1.Cl>[CH3:16][O:15][C:7]1[CH:6]=[C:5]([CH:4]([CH3:18])[C:3]([O:2][CH3:1])=[O:17])[CH:10]=[C:9]([C:11]([F:13])([F:12])[F:14])[CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 86625038Methyl[3-methoxy-5-(trifluoromethyl)phenyl]acetateHCID 178418339Butyllithium

Product 1

HCID 66734169Methyl 2-[3-methoxy-5-(trifluoromethyl)phenyl]propanoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (i) (1.3 g) was added to a pre-formed solution of butyllithium (2.5M in hexanes, 2.51 ml), diisopropylamine (0.88 ml) in dry THF (30 ml) at −78° C. The mixture was kept at −78° C. for 1 hour before adding iodomethane (0.4 ml). The mixture was slowly allowed to warm to room temperature overnight. The mixture was diluted with 2M HCl, extracted with ether, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was purified by flash column chromatography (eluent 2:1 isohexane/diethylether) (0.8 g).

Workup

  1. extractionextracted with ether
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil
  5. customThe oil was purified by flash column chromatography (eluent 2:1 isohexane/diethylether) (0.8 g)

Sources & evidence

ORD record
ord-3ef2069adf84451ab34d3d7c868106b0
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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