Lithium hydroxide, monohydrate → Ethyl-N-(4-carboxyphenoxy)acetimidate

HRID 971182Notes

Reaction equation

HRID 971182 reaction equation
O[Li].O.[CH2:4]([O:6][C:7](=[N:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[CH:13][CH:12]=1)[CH3:8])[CH3:5].C1COCC1.CO.O>O>[CH2:4]([O:6][C:7](=[N:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1)[CH3:8])[CH3:5]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 85420781Ethyl-N-(4-benzyloxycarbonylphenoxy)acetimidate

Product 1

HCID 72965265Ethyl-N-(4-carboxyphenoxy)acetimidateYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LiOH.H2O (550 mg, 13.1 mmol) was added to a solution of ethyl-N-(4-benzyloxycarbonylphenoxy)acetimidate 19 (1.04 g, 3.32 mmol) in a 9/3/3 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 24 h the reaction was diluted with H2O (100 mL), washed with CH2Cl2 (4×30 mL), acidified to pH˜5.0-5.5 with 0.5 N HCl, and extracted with EtOAc (3×30 mL). The combined organics were washed with H2O (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 21 as a white crystalline solid (698 mg, 94%). 1H-NMR (500 MHz, CDCl3) δ 1.37 (t, J=6.9 Hz, 3H), 2.14 (s, 3H), 4.22 (q, J=6.9 Hz, 2H), 7.18-7.22 (m, 2H), 8.04-8.08 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 14.5, 14.6, 63.3, 113.7, 122.1, 132.3, 164.2, 166.7, 172.0; ESI-MS 224 m/z [MH]+, C11H14NO4 requires 224.

Workup

  1. washwashed with CH2Cl2 (4×30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organics were washed with H2O (30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-83267ff5605643518765d41f14996f93
Source dataset
uspto-grants-2007_12
Patent number
US07312361B2

Reaction notes

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