Methyl iodide → ETHYL alpha-METHYL-3-PYRIDYLACETIC ACID

HRID 862448Notes

Reaction equation

HRID 862448 reaction equation
[CH2:1]([CH:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[C:4]([OH:6])=[O:5])[CH3:2].[CH:13]([N-]C(C)C)(C)C.[Li+].C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.CI.ClCl>>[CH2:1]([C:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)([CH3:13])[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 24526ChlorineHCID 2724682Lithium diisopropylamideHCID 179099082-(Pyridin-3-yl)butanoic acidHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 22621946ETHYL alpha-METHYL-3-PYRIDYLACETIC ACIDYield 30%

Procedure

To ethyl 3-pyridylacetic acid (10.86 grams) (65.7 mmoles) was added a 2.0M solution of lithium diisopropylamide in THF/heptane/ethyl benzene (32.87 ml.) (65.8 mmoles) at -30° C. The semi-solid mixture was agitated and sonicated for 1 hour. The mixture was allowed to remain at 25° C. for 1 hour, whereupon methyl iodide (4.09 ml.) (65.7 mmoles) was added. After 1 hour at 25° C. the mixture was taken up in CH2 Cl2 and washed with saturated aqueous sodium bicarbonate and water. The CH2Cl2 was dried (magnesium sulphate), filtered and evaporated to dryness. The residue was chromatographed on silica gel using 10% EtOAc in hexane as the eluant to give the title compound (Yield: 3.48 grams, 30%, MH+ 180).

Workup

  1. customsonicated for 1 hour
  2. additionwas added
  3. washwashed with saturated aqueous sodium bicarbonate and water
  4. dry with materialThe CH2Cl2 was dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel using 10% EtOAc in hexane as the eluant

Sources & evidence

ORD record
ord-5398c0cd3b604f62a092e3863c0d49f5
Source dataset
uspto-grants-1998_02
Patent number
US05719148

Reaction notes

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