Lithium hydroxide, monohydrate → HCID 22282452, compound

HRID 1062663Notes

Reaction equation

HRID 1062663 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([CH2:18][O:19][CH3:20])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH2:18][O:19][CH3:20])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22282425HCID 22282425, compound

Product 1

HCID 22282452HCID 22282452, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(3-cyanophenyl)-5-(methoxymethyl)isoxazole-4-carboxylate (1.12 g, 4.1 mmol) was dissolved in 3 mL THF and 1 mL water. Lithium hydroxide monohydrate (0.20 g, 4.9 mmol) was added and the reaction was allowed to stir for 24 hours under N2. The solvent was removed in vacuo and redissolved in 100 mL of water. The resulting solution was extracted with 30 mL EtOAc twice then acidified with 1N HCl to pH 3. The acidic solution was extracted three times with 30 mL of EtOAc. The combined organic were dried with MgSO4 and concentrated in vacuo to give the desired white solid (0.80 g, 75%). 1H NMR (CDCl3) δ: 7.98 (m, 1H); 7.91 (dd, J=8.1, 2.9, 1H); 7.79 (dd, J=8.1 , 2.9, 1H); 7.59 (t, J=8.1, 1H); 4.89 (s, 2H); 3.53 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionredissolved in 100 mL of water
  3. extractionThe resulting solution was extracted with 30 mL EtOAc twice
  4. extractionThe acidic solution was extracted three times with 30 mL of EtOAc
  5. dry with materialThe combined organic were dried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7988bb5dafd54f4c9ddbac73ed440c77
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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