Diisobutylaluminumhydride → HCID 178520861, compound

HRID 658102Notes

Reaction equation

HRID 658102 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:35])[C:10](=[C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27]2)[C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:35])[C:10](=[C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[NH:30]2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH:20][CH2:21][OH:22])[CH:14]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 178470912HCID 178470912, compound

Product 1

HCID 178520861HCID 178520861, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 25 ml portion of THF solution containing 1.2 g of ethyl 3-{3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}acrylate was cooled to −78° C. in a stream of argon gas, 5.5 ml of 1.0 M diisobutylaluminum hydride-Tol solution was gradually added dropwise thereto, and then the mixture was stirred at 0° C. for about 2 hours. This was again cooled to −78° C. the same amount of the reducing agent was added dropwise thereto, and then the mixture was gradually risen to room temperature and stirred for about 40 minutes. The reaction liquid was cooled to −30° C. or lower, small amount of methanol and purified water were added thereto, and the thus formed insoluble matter was removed by filtration through washing with an appropriate amount of ethyl acetate. The organic layer obtained by layer separation operation of the filtrate was washed with water, dried with anhydrous magnesium sulfate and concentrated, and then the thus obtained residue was purified by a silica gel column chromatography to obtain 0.58 g (53%) of 1-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-[3-(3-hydroxyprop-1-en-1-yl)phenyl]propane-1,3-dione as a yellow foam from a ethyl acetate-hexane (1:1) eluate. FA: 433

Workup

  1. additionwas gradually added dropwise
  2. temperatureThis was again cooled to −78° C. the same amount of the reducing agent
  3. additionwas added dropwise
  4. customwas gradually risen to room temperature
  5. stirringstirred for about 40 minutes
  6. customThe reaction liquid
  7. temperaturewas cooled to −30° C.
  8. customlower, small amount of methanol and purified water
  9. additionwere added
  10. customthe thus formed insoluble matter was removed by filtration
  11. washthrough washing with an appropriate amount of ethyl acetate
  12. customThe organic layer obtained by layer separation operation of the filtrate
  13. washwas washed with water
  14. dry with materialdried with anhydrous magnesium sulfate
  15. concentrationconcentrated
  16. customthe thus obtained residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-8b86cdfaf6594cd7984b25177a353778
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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