Sodium Hydroxide → HCID 66759943, compound

HRID 1850407Notes

Reaction equation

HRID 1850407 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Br:11][C:12]1[C:13]([CH3:25])=[CH:14][C:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17](=O)[C:16]=2[C:23]=1[CH3:24].[OH-].[Na+]>O.C1COCC1>[Br:11][C:12]1[C:13]([CH3:25])=[CH:14][C:15]2[O:19][C:18]([CH3:20])([CH3:21])[CH2:17][C:16]=2[C:23]=1[CH3:24]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23114306HCID 23114306, compound

Product 1

HCID 66759943HCID 66759943, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (2.33 mg, 61.5 mmol) was added to a suspension of THF (70 mL) containing aluminium chloride (8.20 g, 6.15 mmol) under ice-cooling condition, and the mixture was stirred for 15 minutes. After that, a solution of THF (30 mL) containing 5-bromo-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (6.63 g, 24.6 mmol) synthesized in Reference Example 119 was added thereto, and the mixture was stirred under heated reflux for 2.5 hours. The reaction solution was iced, and after that, water was added dropwise thereto. 0.5N sodium hydroxide aqueous solution was further added thereto, and the mixture was stirred at room temperature for 10 minutes. Insolubles were removed by filtration. The filtrate was subjected to extraction using a mixed solvent of ethyl acetate-diethyl ether (1:1). The extract was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 9:1). Crystallization was performed using methanol-ethyl acetate to give 5.29 g of the title compound (yield: 84%).

Workup

  1. temperaturecooling condition
  2. customsynthesized in Reference Example 119
  3. additionwas added
  4. stirringthe mixture was stirred
  5. temperatureunder heated
  6. temperaturereflux for 2.5 hours
  7. stirringthe mixture was stirred at room temperature for 10 minutes
  8. customInsolubles were removed by filtration
  9. extractionThe filtrate was subjected to extraction
  10. washThe extract was washed with saturated saline
  11. customdried
  12. customThe solvent was removed under reduced pressure
  13. customthe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 9:1)
  14. customCrystallization

Sources & evidence

ORD record
ord-10fe3e3ddb7a4fc5b445322794744fb8
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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