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

HRID 48157

Reaction equation

HRID 48157 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1.CI>O1CCCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]([CH3:1])[C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 90266Methyl 4-methoxyphenylacetateHCID 2724682Lithium diisopropylamide

Product 1

HCID 12398855Methyl 2-(4-methoxyphenyl)propanoateYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of lithium diisopropylamide (2.0M solution in tetrahydrofuran/ethylbenzene/heptane, 34.0 ml, 0.0667 mol) was added dropwise to a solution of methyl 4-methoxyphenylacetate (12.0 g, 0.0667 mol) in tetrahydrofuran (150 ml) at −70° C. under a nitrogen atmosphere and the mixture was stirred at −70° C. for 1 hour. A solution of methyl iodide (9.5 g, 0.0667 mol) in tetrahydrofuran (20 ml) was added dropwise and the mixture was stirred at −70° C. for a further 1 hour. The cooling bath was removed and the mixture was allowed to warm to room temperature overnight. The reaction was quenched with water, acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:hexane 1:9, to give methyl 2-(4-methoxyphenyl)propionate (8.8 g) as a colourless oil.

Workup

  1. stirringthe mixture was stirred at −70° C. for a further 1 hour
  2. customThe cooling bath was removed
  3. temperatureto warm to room temperature overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate was evaporated in vacuo
  11. customThe residue was purified by flash column chromatography on silica gel
  12. washeluting with ethyl acetate:hexane 1:9

Sources & evidence

ORD record
ord-20dc3787e2554ade8696e1d056a31d78
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Linked notes

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