Lithium Hydroxide → (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylic acid hydrate

HRID 322855Notes

Reaction equation

HRID 322855 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1/[CH:23]=[C:24](\[C:29]#[N:30])/[C:25]([O:27]C)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1>[OH2:8].[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1/[CH:23]=[C:24](\[C:29]#[N:30])/[C:25]([OH:27])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86756581methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate

Product 1

HCID 70226070(E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylic acid hydrateYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate (400 mg) in tetrahydrofuran (20 mL) containing 0.5 N aqueous lithium hydroxide solution (4 mL) is stirred at ambient temperature for 2 hours. The reaction is concentrated under reduced pressure and the residue taken up in water. This solution is acidified to pH 1 and extracted with diethyl ether. The organic layer is dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylic acid hydrate as a yellow solid (30 mg). [Elemental analysis:- C, 71.43; H, 5.25; N, 3.47%; Calculated for C24H19NO4.H2O:- C, 71.40; H, 4.81; N, 3.72%].

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2fb53a59c234f09be444f947905bea0
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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