Methyl iodide → Methyl 2-(pyridin-2-yl)propanoate

HRID 2203305Notes

Reaction equation

HRID 2203305 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[Li+].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH3:13])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 74264Methyl 2-pyridylacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 54595201Methyl 2-(pyridin-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-pyridylacetate (6.81 mL, 50 mmol) was added dropwise to LHMDS (1.0M in THF, 50 mL) and THF (65 mL) cooled to 0° C. After 30 minutes iodomethane (3.97 g, 63.5 mmol) was added to the solution. After stirring for 1 hour at 0° C. the solution was concentrated and the residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CHCl3-d): δ 8.56 (d, J=4.9 Hz, 1H); 7.66 (td, J=7.6, 1.8 Hz, 1H); 7.18 (dd, J=7.6, 4.9 Hz, 1H); 3.96 (q, J=7.2 Hz, 1H); 3.69 (s, 3H). 1.56 (d, J=7.2 Hz, 3H). m/z 166.5 (M+H).

Workup

  1. concentrationwas concentrated
  2. customthe residue was purified by silica gel chromatography
  3. customto give the indicated product

Sources & evidence

ORD record
ord-7037350d604b4e7099140fd7087e4c6e
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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