Diisobutylaluminum hydride → HCID 68162254, compound

HRID 2400326Notes

Reaction equation

HRID 2400326 reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[CH:14][N:15]=[C:9]2[CH:8]=1)C.[H-].C([Al+]CC(C)C)C(C)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.ClCCl>[N:15]1[CH:14]=[CH:13][N:10]2[CH:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[CH2:4][OH:3])=[CH:8][C:9]=12

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 21225700DiisobutylaluminumhydrideHCID 67029394HCID 67029394, compound

Product 1

HCID 68162254HCID 68162254, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 21877217Toluene methylene chlorideSolvent

Procedure

(E)-3-Imidazo[1,2-a]pyridin-7-yl-acrylic acid ethyl ester (prepared according to Procedure H1 to H4 using triethylphosphono acetate, 519 mg, 2.4 mmol) was dissolved in a mixture of toluene/dichloromethane (1:1, 12 ml) and cooled on a dry ice/acetone bath. Diisobutylaluminium hydride (1 M in toluene, 3 ml) was added dropwise. After 45 minutes the reaction was transferred to a salt/ice bath and further portions of DIBAL were added until the reaction was complete. The reaction was quenched by the cautious addition of methanol and was allowed to warm to room temperature. The reaction was concentrated in vacuo and 2N sodium hydroxide solution was added. This was extracted twice with dichloromethane and the combined liquors were dried and concentrated to furnish the desired monomer (327 mg) as a yellow solid MS: [M+H]+=175

Workup

  1. temperaturecooled on a dry ice/acetone bath
  2. additionwere added until the reaction
  3. customThe reaction was quenched by the cautious addition of methanol
  4. concentrationThe reaction was concentrated in vacuo and 2N sodium hydroxide solution
  5. additionwas added
  6. extractionThis was extracted twice with dichloromethane
  7. customthe combined liquors were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f4e2e35882584dfa884325a61c1a68f8
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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