Diisobutylaluminum hydride → HCID 11401661, compound

HRID 1744929Notes

Reaction equation

HRID 1744929 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]3[CH:11]=[C:10]([C:12](OCC)=[O:13])[N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:12]([C:10]1[N:9]=[C:7]2[N:6]([CH:11]=1)[C:5]1[CH:17]=[CH:18][C:2]([CH3:1])=[CH:3][C:4]=1[S:8]2)=[O:13]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 638597HCID 638597, compound

Product 1

HCID 11401661HCID 11401661, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of Ethyl 7-methylimidazo[2,1-b]-benzthiazole-2-carboxylate (4.0 g, 15.38 mmol) in dry THF at −78° C., DIBAL (1M. solution in toluene) (16.0 ml, 16 mmol) was added. The reaction mixture was stirred at −78° C. and slowly elevated to room temperature. The reaction mixture was stirred at room temperature for 30 minutes and quenched with saturated NH4Cl. The reaction mixture was extracted with chloroform and washed well with water. The organic layer was dried over anhydrous MgSO4; filtered and concentrated. The residue was purified bt SiO2 column chromatography by eluting it with chloroform: metrhanol (20:1). Brown solid; (M+H) 217; Yield: 800 mg (24%)

Workup

  1. customslowly elevated to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. customquenched with saturated NH4Cl
  4. extractionThe reaction mixture was extracted with chloroform
  5. washwashed well with water
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified bt SiO2 column chromatography
  10. washby eluting it with chloroform

Sources & evidence

ORD record
ord-286a2c74bfca4a68be7f2fef39a58ae3
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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