Tetrahydrofuran → HCID 21866772, compound

HRID 1794244Notes

Reaction equation

HRID 1794244 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[N:15][C:14]=1[CH2:25][C:26]1[CH:27]=[C:28]([CH:41]=[CH:42][CH:43]=1)[CH2:29][CH:30]([C:36](OCC)=[O:37])[C:31](OCC)=[O:32].[OH-].[Na+]>O>[CH3:12][C:13]1[O:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)=[N:15][C:14]=1[CH2:25][C:26]1[CH:27]=[C:28]([CH:41]=[CH:42][CH:43]=1)[CH2:29][CH:30]([CH2:36][OH:37])[CH2:31][OH:32]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69590757HCID 69590757, compound

Product 1

HCID 21866772HCID 21866772, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 30 ml of dry tetrahydrofuran, 854 mg of lithium aluminium hydride was added, and 3.94 g of diethyl 3-{[5-methyl-2-(p-tolyl)oxazol-4-yl]methyl}benzylmalonate/10 ml of dry tetrahydrofuran was added dropwise with stirring under ice-cooling. The mixture was stirred for 1.5 hours at room temperature and cooled with ice-cold water. To the mixture were added dropwise 0.85 ml of water, 0.85 ml of 15% sodium hydroxide solution and 2.5 ml of water sequentially, and stirred for 15 minutes. The mixture was filtrated to remove insolubles, and the filtrate was concentrated. The residue was dissolved into ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=20:1) to provide 2.32 g of the objective compound as colorless crystals. M.p. 114–115° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1.5 hours at room temperature
  3. temperaturecooled with ice-cold water
  4. stirringstirred for 15 minutes
  5. filtrationThe mixture was filtrated
  6. customto remove insolubles
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe residue was dissolved into ethyl acetate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-7cdccc616dca43d984122cf42d28eae8
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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