Lithium hydroxide, monohydrate → HCID 86648424, compound

HRID 2387411Notes

Reaction equation

HRID 2387411 reaction equation
C[O:2][C:3]([C:5]1([CH3:25])[O:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:7][O:6]1)=[O:4].O[Li].O>O1CCCC1.CO.O>[CH3:25][C:5]1([C:3]([OH:4])=[O:2])[O:6][CH2:7][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:9][O:10]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86648421HCID 86648421, compound

Product 1

HCID 86648424HCID 86648424, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of. Methyl-2-methyl-5-[4-(1-phenyl-ethylideneaminooxy)-butyl]-[1,3]dioxane-2-carboxylate (prepared as per example 1) (1.38 g) in a mixture of tetrahydrofuran and methanol was added another solution of LiOH.H2O (332 mg) in water and the reaction mixture was stirred at ambient temperature for about 18 hours. Solvent was evaporated under reduced pressure, water was added to the residue, acidified with 1N HCl to pH 6 and extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure. Crude product was chromatographed (flash) over silica-gel using 25% ethyl acetate in hexane as an eluent to obtain 1 g of pure product.

Workup

  1. customSolvent was evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with water, brine solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customCrude product was chromatographed (flash) over silica-gel

Sources & evidence

ORD record
ord-bf5b66f8451a4004999a070c2c5d8176
Source dataset
uspto-grants-2012_09
Patent number
US08268867B2

Reaction notes

Loading…