Methyl iodide → Methyl 2-(3-nitrophenyl)propanoate

HRID 15845Notes

Reaction equation

HRID 15845 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[N+:11]([C:14]1[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].I[CH3:26].[Cl-].[NH4+]>C1COCC1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]([CH3:26])[C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 526967Methyl 2-(3-nitrophenyl)acetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 13054272Methyl 2-(3-nitrophenyl)propanoateYield 33.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hexamethyldisilazide (1M, hexane, 1.0 eq., 21.5 ml) was added dropwise to a stirred solution of methyl (3-nitrophenyl)acetate (4.2 g) in THF (30 ml) at −30 C. The mixture was warmed to 0 C and re-cooled to −30 C then iodomethane (1.0 equiv., 3.0 g.) was added. The solution was warmed to room temperature and poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The crude was purified using chromatography (SiO2, SPE) using cyclohexane/ethyl acetate (80/20) as eluent to afford the title compound as yellow liquid (1.50 g, 30% yield).

Workup

  1. temperatureThe mixture was warmed to 0 C
  2. temperaturere-cooled to −30 C
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude was purified

Sources & evidence

ORD record
ord-eab3a07efa654e14a99efe66be30d9ab
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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