Methyl iodide → (S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hexanoic acid

HRID 1643272Notes

Reaction equation

HRID 1643272 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:20])[CH2:11][C@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1.[CH3:21]I>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]([O:20][CH3:21])[CH2:11][C@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59568771(S)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hexanoic acid

Product 1

HCID 59568810(S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (129 mg, 60% oil dispersion) in 20 mL THF was slowly added at room temperature the crude (S)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hexanoic acid isolated above as a solution in 10 mL THF. To this mixture was added dropwise methyl iodide (164 mL, 373.9 mg, 2.6 mmol) and the resulting stirred for 3 h at room temperature. The reaction was quenched by the slow addition of 15 mL 1M aqueous HCl and the mixture extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent afforded the product as an oil which was used directly in the next reaction without further purification.

Workup

  1. customThe reaction was quenched by the slow addition of 15 mL 1M aqueous HCl
  2. extractionthe mixture extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-4be34f7f837b449aa400ff8bdb06335b
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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