Water → 1-(2-hydroxyethyl)-2,3-dihydro-1H-imidazo[1,2-b]pyrazole

HRID 2380288Notes

Reaction equation

HRID 2380288 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][N:13]1[C:20]2[N:16]([N:17]=[CH:18][CH:19]=2)[CH2:15][CH2:14]1)=O)C.[F-].[Na+].O>O1CCCC1>[OH:9][CH2:10][CH2:12][N:13]1[C:20]2[N:16]([N:17]=[CH:18][CH:19]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 189552941-ethoxycarbonylmethyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 150777341-(2-hydroxyethyl)-2,3-dihydro-1H-imidazo[1,2-b]pyrazoleYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of lithium aluminum hydride (3.89 g) in tetrahydrofuran (195 ml) was added dropwise a solution of 1-ethoxycarbonylmethyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (20 g) in tetrahydrofuran (100 ml) at room temperature. The mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled under ice-bath. To a mixture were added sodium fluoride (17.2 g) and water (5.5 ml) under ice-cooling. The insoluble material was filtered off and the filtrate was evaporated. The residue was subjected to column chromatography on silica gel using ethyl acetate as an eluent. Fractions containing the object compound were combined and evaporated in vacuo to give 1-(2-hydroxyethyl)-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (5.91 g).

Workup

  1. temperatureThe reaction mixture was cooled under ice-bath
  2. temperaturecooling
  3. filtrationThe insoluble material was filtered off
  4. customthe filtrate was evaporated
  5. additionFractions containing the object compound
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6796db5375a0432db7d06f8cbf4e62fc
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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