Propylene Oxide → HCID 21196589, compound

HRID 1066886Notes

Reaction equation

HRID 1066886 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[N:2]1.[H-].[Na+].[CH2:15]1[O:18][CH:16]1[CH3:17]>CN(C)C=O>[N:1]1([CH2:15][CH:16]([OH:18])[CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 211966031H-Furo[2,3-g]indazole

Product 1

HCID 21196589HCID 21196589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under argon atmosphere, a dimethylformamide (5 ml) solution containing 1.00 g of 1H-furo(2,3-g]indazole was added dropwise to a dimethylformamide (10 ml) solution containing 0.27 g of sodium hydride under cooling with ice-bath, and the mixture was stirred for 30 minutes. A 0.52 ml of propylene oxide was added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 41 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed with brine and then dried with anhydrous magnesium sulfate. After removal of the solvent, the residue was purified by a silica gel column chromatography to give 0.59 g of 1-(1H-furo[2,3-g]indazol-1-yl)propan-2-ol.

Workup

  1. temperatureunder cooling with ice-bath
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 41 hours
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-e2fcb1f895714cea832f9e0e86a98aba
Source dataset
uspto-grants-2001_06
Patent number
US06245796B1

Reaction notes

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