Methyl iodide → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

HRID 1643282Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 217 mg NaH in 20 mL THF was added (S)-2-((R)-2-(4-fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid in 5 mL THF slowly at room temperature. To this mixture was added methyl iodide (289 μL) dropwise followed by stirring for 3 h at 25° C. The reaction was quenched by the addition of 10 mL 1M HCl and then extracted with ethylacetate (3×30 mL). The combined organic layers were washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent afforded an oil which was used without further purification in the next reaction.

Workup

customThe reaction was quenched by the addition of 10 mL 1M HCl
extractionextracted with ethylacetate (3×30 mL)
washThe combined organic layers were washed with brine (2×20 mL)
dry with materialdried over sodium sulfate
customEvaporation of solvent
customafforded an oil which
customwas used without further purification in the next reaction

Sources & evidence

ORD record: ord-9d82caf123ad422a898567ab32e2940e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119692B2

Reaction notes

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