Tetrahydrofuran → HCID 135966103, compound

HRID 2380286Notes

Reaction equation

HRID 2380286 reaction equation
C(O[C:4]([C:6]1[CH:10]=[N:9][N:8]2[CH2:11][CH2:12][NH:13][C:7]=12)=O)C.[H-].COCCO[Al+]OCCOC.[Na+].[H-].O1CCCC1>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[CH3:4][C:6]1[CH:10]=[N:9][N:8]2[CH2:11][CH2:12][NH:13][C:7]=12

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 136156080HCID 136156080, compound

Product 1

HCID 135966103HCID 135966103, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

To a solution of 2,3-dihydro-7-ethoxycarbonyl-1H-imidazo[1,2-b]pyrazole (5 g) in xylene (27 ml) was added dropwise 3.4M solution (27 ml) of sodium bis(2-methoxyethoxy)aluminum hydride in toluene under ice-cooling. The mixture was stirred at room temperature and then stirred at 140° C. for 3.5 hours. The reaction mixture was cooled at 5° C. and poured into a mixture of ice-water (100 ml) and tetrahydrofuran (100 ml). The insoluble material was filtered off and the filtrate was separated. The aqueous layer was extracted with tetrahydrofuran. The organic layer and extract were combined and dried over magnesium sulfate. The solvent was evaporated to give 2,3-dihydro-7-methyl-1H-imidazo[1,2-b]pyrazole (2.04 g).

Workup

  1. temperaturecooling
  2. stirringstirred at 140° C. for 3.5 hours
  3. temperatureThe reaction mixture was cooled at 5° C.
  4. filtrationThe insoluble material was filtered off
  5. customthe filtrate was separated
  6. extractionThe aqueous layer was extracted with tetrahydrofuran
  7. extractionThe organic layer and extract
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9c32f374a81f4cb39a5c1ddaa9774ddb
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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