Methyl iodide → 1374320-98-5

HRID 2408205Notes

Reaction equation

HRID 2408205 reaction equation
[H-].[Na+].[OH:3][CH:4]([CH2:8][S:9][CH3:10])[C:5]([OH:7])=[O:6].I[CH3:12]>CN(C=O)C>[CH3:12][O:3][CH:4]([CH2:8][S:9][CH3:10])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156476672-Hydroxy-3-(methylsulfanyl)propanoic acid

Product 1

HCID 866646881374320-98-5Yield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of sodium hydride (0.176 g, 4.41 mmol) in DMF (5 mL) was added a solution of 2-hydroxy-3-(methylthio)propanoic acid (0.25 g, 1.836 mmol) in 1 mL DMF at 25° C. and stirred for 10 min Vigorous bubbling was observed upon addition of NaH. Then iodomethane (0.126 mL, 2.020 mmol) was added and the solution was stirred at 25° C. overnight. The reaction was quenched by addition of 2 N HCl, extracted with 3×10 mL of EtOAc, the combined organic layers were washed with water (2×20 mL), concentrated and purified by column chromatography, eluted with 0-100% EtOAc/hexane, gave 2-methoxy-3-(methylthio)propanoic acid (126 mg, 0.839 mmol, 45.7% yield) as colorless oil: 1H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 4.03 (dd, J=6.9, 4.4 Hz, 1H), 3.51 (s, 3H), 2.98-2.93 (m, 1H), 2.86 (dd, J=14.1, 6.9 Hz, 1H), 2.21 (s, 3H); EIMS m/z 150.

Workup

  1. customVigorous bubbling
  2. additionwas observed upon addition of NaH
  3. stirringthe solution was stirred at 25° C. overnight
  4. customThe reaction was quenched by addition of 2 N HCl
  5. extractionextracted with 3×10 mL of EtOAc
  6. washthe combined organic layers were washed with water (2×20 mL)
  7. concentrationconcentrated
  8. custompurified by column chromatography
  9. washeluted with 0-100% EtOAc/hexane

Sources & evidence

ORD record
ord-5391a03a53594943b95b349163106221
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

Loading…