Methyl iodide → Methyl 2-(4-chloro-3-methoxyphenyl)propanoate

HRID 1686382Notes

Reaction equation

HRID 1686382 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH3:13])[CH:6]=1.[Li][CH2:16]CCC.C(NC(C)C)(C)C.CI>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]([CH3:16])[C:3]([O:2][CH3:1])=[O:14])=[CH:6][C:7]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 57609448Methyl(4-chloro-3-methoxyphenyl)acetateHCID 178418339Butyllithium

Product 1

HCID 67266387Methyl 2-(4-chloro-3-methoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (i) (0.5 g) was added to a solution of nBuLi (1.75 ml, 1.6 M in THF) and diisopropylamine (0.4 ml) in THF (10 ml) at −78° C. and stirred for 1 h, then methyl iodide (0.18 ml) was added, stirred for 1 h at −78° C. then at room temperature for 1 h and quenched with water. The product was extracted with ether, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 1:1 isohexane/ether) to give the subtitle compound (0.21 g).

Workup

  1. stirringstirred for 1 h at −78° C.
  2. waitat room temperature for 1 h
  3. customquenched with water
  4. extractionThe product was extracted with ether
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography (eluent 1:1 isohexane/ether)

Sources & evidence

ORD record
ord-2bcc2a2437734035b43297109a5c9e68
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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