Methyl iodide → (R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

HRID 1643264Notes

Reaction equation

HRID 1643264 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17].[CH3:18]I>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([O:16][CH3:18])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42077386(R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid

Product 1

HCID 59568829(R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of NaH (373 mg of a 60% dispersion in mineral oil, 9.3 mmol) in 20 mL THF was slowly added (R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid as a solution in 10 mL THF at 25° C. Methyl iodide (974 mg, 6.9 mmol, 427 μL) was then added dropwise to the mixture. The resulting mixture was stirred for 3 h at room temperature and then the reaction was quenched by the addition of 20 mL of 1M HCl. The mixture was and extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil which was used in the next step without further purification.

Workup

  1. customat 25° C
  2. customthe reaction was quenched by the addition of 20 mL of 1M HCl
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washthe combined organic layers washed with brine (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of solvent
  7. waitleft the crude product as an oil which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-aecb9b0a7df74de593857e3ba316a2c8
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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