Methanol → (S)-Methyl 2-((R)-2-(4-fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoate

HRID 1643283Notes

Reaction equation

HRID 1643283 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:17][CH3:18])[CH2:9][C@H:10]([CH2:14][CH:15]=[CH2:16])[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:19].OS(O)(=O)=O.[CH3:25]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:17][CH3:18])[CH2:9][C@H:10]([CH2:14][CH:15]=[CH2:16])[C:11]([O:13][CH3:25])=[O:12])=[CH:4][C:3]=1[CH3:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59568837(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

Product 1

HCID 59568824(S)-Methyl 2-((R)-2-(4-fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoate

Procedure

To a solution of (5)-2((R)-2-(4-fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid in 5 mL methanol was added concentrated H2SO4 (50 mL) at room temperature and the resulting solution stirred for 16 h. The reaction mixture was concentrated under reduced pressure, the residue treated with water, and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×10 mL) and dried over Na2SO4. The product was isolated by flash column chromatography eluting with 0% to 10% ethyl acetate/hexane gradient solvent to give 122 mg of the title compound as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue treated with water
  3. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers were washed with brine (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. customThe product was isolated by flash column chromatography
  7. washeluting with 0% to 10% ethyl acetate/hexane gradient solvent

Sources & evidence

ORD record
ord-ac223c4fc8ba41d280b2db51cc2111eb
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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