Sodium Hydroxide → HCID 59485025, compound

HRID 1850428Notes

Reaction equation

HRID 1850428 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][N:12]([CH3:47])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]3[C:25](=O)[C:26]([CH3:29])([CH3:28])[O:27][C:23]=3[C:22]([CH3:31])=[C:21]([CH3:32])[C:20]=2[N:33]2[CH2:38][CH2:37][N:36]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[CH2:35][CH2:34]2)=[CH:15][CH:14]=1.[OH-].[Na+]>O.C1COCC1>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([N:36]2[CH2:35][CH2:34][N:33]([C:20]3[C:21]([CH3:32])=[C:22]([CH3:31])[C:23]4[O:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]=4[C:19]=3[C:16]3[CH:15]=[CH:14][C:13]([N:12]([CH3:11])[CH3:47])=[CH:18][CH:17]=3)[CH2:38][CH2:37]2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66760364HCID 66760364, compound

Product 1

HCID 59485025HCID 59485025, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the THF (15 mL) suspension of lithium aluminum hydride (342 mg, 9.00 mmol), aluminum chloride (1.20 g, 9.00 mmol) was added under ice cooling, and then the mixture was stirred for 10 minutes and added with the THF (25 mL) solution of 4-[4-(dimethylamino)phenyl]-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (1.50 g, 3.00 mmol) synthesized in Reference example 31, followed by further stirring for 2.5 hours under reflux. After cooling the mixture solution on ice, water was added dropwise thereto and 0.5 N aqueous solution of sodium hydroxide was further added. The mixture was stirred for 10 minutes at room temperature. Undissolved residues were removed by filtration. The filtrate was extracted with the mixture solvent of ethyl acetate-ether (1:1). After washing with the saturated brine, the extract solution was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate 96:4-85:15) and crystallized from ethyl acetate and hexane to obtain the title compound 1.01 g (yield 69%). Melting point was 177 to 179° C. (ethyl acetate-hexane).

Workup

  1. additionwas added under ice cooling
  2. customsynthesized in Reference example 31
  3. stirringby further stirring for 2.5 hours
  4. temperatureunder reflux
  5. additionwas added dropwise
  6. stirringThe mixture was stirred for 10 minutes at room temperature
  7. customwere removed by filtration
  8. extractionThe filtrate was extracted with the mixture solvent of ethyl acetate-ether (1:1)
  9. washAfter washing with the saturated brine
  10. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate 96:4-85:15)
  13. customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-5e9405a6a5f647e8820bc39419ad73c4
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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