3-(3-Benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester → 3-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester

HRID 459312Notes

Reaction equation

HRID 459312 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([O:20][CH3:21])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1>CO>[CH3:1][O:2][C:3](=[O:22])[CH:4]([O:20][CH3:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 694217553-(3-Benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester

Product 1

HCID 588226203-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(3-benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester (Example 291, Step 2) (3.96 g) in methanol (10 mL) was placed in a round bottom flask equipped with a reflux condenser. The mixture was cooled to 0° C. and Mg turnings (6.45 g) were added. The mixture was initially stirred vigorously and then further stirred at room temperature for about an hour. The solvent was evaporated under vacuum, and 100 mL of diethyl ether were added to the resulting solid. HCl (3N, 100 mL) was added and the solution was stirred for one minute. The organic layer was separated from the slurry, and 100 mL of diethyl ether and HCl (3N, 100 mL) were added to the remaining slurry. The procedure was repeated until the entire solid was dissolved. The combined ethereal extracts were washed with brine and dried over MgSO4. Concentration of the mixture afforded a yellow oil which was about 90% pure bye NMR. 1H-NMR (CDCl3, 200.15 MHz): 7.45–7.17 (m, 6H), 6.88–6.81 (m, 3H), 5.05 (s, 2H), 3.97 (dd, 1H, J=7.3, 5.4), 3.72 (s, 3H), 3.34 (s, 3H), 3.00 (d, 1H, J=5.1), 2.99 (d, 1H, J=7.8).

Workup

  1. customequipped with a reflux condenser
  2. stirringfurther stirred at room temperature for about an hour
  3. customThe solvent was evaporated under vacuum, and 100 mL of diethyl ether
  4. additionwere added to the resulting solid
  5. additionHCl (3N, 100 mL) was added
  6. stirringthe solution was stirred for one minute
  7. customThe organic layer was separated from the slurry, and 100 mL of diethyl ether and HCl (3N, 100 mL)
  8. additionwere added to the remaining slurry
  9. dissolutionwas dissolved
  10. washThe combined ethereal extracts were washed with brine
  11. dry with materialdried over MgSO4
  12. customConcentration of the mixture afforded a yellow oil which

Sources & evidence

ORD record
ord-151b87ce810c4da7bce2161262e618ea
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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