Hydrochloric Acid → (E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate

HRID 1619158Notes

Reaction equation

HRID 1619158 reaction equation
[CH:1]([C:3]1[C:24]([CH3:25])=[CH:23][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])=[C:5]([CH3:26])[CH:4]=1)=[O:2].[CH2:27]([Mg]Br)[CH3:28].Cl>O1CCCC1.O>[OH:2][CH:1]([C:3]1[C:24]([CH3:25])=[CH:23][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])=[C:5]([CH3:26])[CH:4]=1)[CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86666585(E)-methyl 2-(2-((4-formyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylateHCID 178418443HCID 178418443, compound

Product 1

HCID 67954688(E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylateYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.2 g (0.56 mmol) of (E)-methyl 2-(2-((4-formyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 1 in 15 mL of tetrahydrofuran (THF) was refrigerated at −78° C. and reacted at that temperature for 2 hours with ethyl magnesium bromide (0.22 mL, 1.2 eq) while stirring. After completion of the reaction, the reaction mixture was adjusted to pH 7 at 0° C. with 1N-HCl and concentrated in a vacuum. The residue thus obtained was stirred in water (10 mL) and extracted twice with 10 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated in a vacuum to remove the solvent. The concentrate was purified by silica gel chromatography to yield (E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white oil (0.17 g, yield 79%).

Workup

  1. customwas refrigerated at −78° C.
  2. customAfter completion of the reaction
  3. concentrationconcentrated in a vacuum
  4. customThe residue thus obtained
  5. extractionextracted twice with 10 mL of dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated in a vacuum
  9. customto remove the solvent
  10. customThe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-caab5bb3f66743bc968db2132c17327b
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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