Tetrahydrofuran → HCID 14673953, compound

HRID 1199424Notes

Reaction equation

HRID 1199424 reaction equation
[CH3:1][C:2]1([CH3:20])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH:15][C:16](=[O:18])[CH3:17])[CH:3]1O)=[N:10][O:11][N:12]=3.O1CCCC1.[H-].[Na+]>O>[CH3:1][C:2]1([CH3:20])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[C:4]([NH:15][C:16](=[O:18])[CH3:17])=[CH:3]1)=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 14673922HCID 14673922, compound

Product 1

HCID 14673953HCID 14673953, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 80 mg (0.289 m mol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-acetylamino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole and 5 ml of dried tetrahydrofuran were added 25 mg of sodium hydride (oil, content of more than 55%) with stirring for 1 hour at the room temperature. After the mixture was carefully added with water and extracted thrice with ethyl acetate. The combined ethyl acetate layer was washed successively with 0.5N hydrochloric acid, water and saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was subjected to a preparative thin layer column chromatography using a developing solvent of ethyl acetate-methanol (10:1 (v/v)) to obtain 24 mg (yield: 32%) of the intended compound. The obtained compound was recrystallized from ethanol to obtain the pure intended compound.

Workup

  1. extractionextracted thrice with ethyl acetate
  2. washThe combined ethyl acetate layer was washed successively with 0.5N hydrochloric acid, water and saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-bcf5658fe8fb49eebd183b0627b26192
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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