Methyl iodide → (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoic acid

HRID 1643289Notes

Reaction equation

HRID 1643289 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]=[CH:13][CH2:14][C@@H:15]([CH2:19][C@H:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[OH:21])[C:16]([OH:18])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:29]I>C1COCC1>[CH2:3]([O:10][CH2:11][CH:12]=[CH:13][CH2:14][C@@H:15]([CH2:19][C@H:20]([C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[O:21][CH3:29])[C:16]([OH:18])=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66754740(S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid

Product 1

HCID 66755200(S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (605 mg, 60% oil dispersion) in 30 mL THF was slowly added at room temperature the crude (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid isolated above as a solution in 5 mL THF. To this mixture was added dropwise methyl iodide (732 μL, 1.7 g, 11.3 mmol) and the resulting stirred for 3 h at room temperature. The reaction was quenched by the slow addition of 20 mL 1M aqueous HCl and the mixture extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (2×30 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 20 mL 1M aqueous HCl
  2. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (2×30 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-6daabbd077ea4b189ac8287936bea2a1
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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