Methanol → (S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoate

HRID 1643290Notes

Reaction equation

HRID 1643290 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][C@@H:13]([CH2:17][C@H:18]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[O:19][CH3:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:33]O>>[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][C@@H:13]([CH2:17][C@H:18]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[O:19][CH3:20])[C:14]([O:16][CH3:33])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 66755200(S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoic acid

Product 1

HCID 66754419(S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoate

Procedure

To a solution of ((S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoic acid in 10 mL methanol was added concentrated H2SO4 (150 μL) at room temperature and the resulting solution stirred for 8 h. The reaction mixture was concentrated under reduced pressure, the residue treated with water, and the mixture was extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×30 mL) and dried over Na2SO4. The product was isolated by flash column chromatography eluting with 0% to 20% ethyl acetate/hexane gradient solvent to give 494 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 (3×40 mL)
  4. washThe combined organic layers were washed with brine (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. customThe product was isolated by flash column chromatography
  7. washeluting with 0% to 20% ethyl acetate/hexane gradient solvent

Sources & evidence

ORD record
ord-1a30f5a36bf14e5895d754aaf5f41157
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

Loading…