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Diisobutylaluminumhydride → HCID 22010670, compound

HRID 323173
Notes
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Reaction equation

HRID 323173 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:41]=[CH:40][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][C:34](OCC)=[O:35])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH:34]=[O:35])=[O:22])=[CH:40][CH:41]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 22010702HCID 22010702, compound

Product 1

HCID 22010670HCID 22010670, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-ethoxycarbonylprop-1-yloxy)phenyl]benzamide (1.10 g) in dichloromethane (20 ml) was added dropwise a solution of diisobutylaluminum hydride in toluene (1.5 M solution, 2 ml) at −78° C. and the mixture was stirred at the same temperature for 2 hours. The reaction was quenched with addition of water and the resulting mixture was warmed to ambient temperature. The mixture was extracted with dichloromethane and the organic phase was washed successively with 1N hydrochloric acid, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-formylprop-1-yloxy)phenyl]benzamide (987 mg) as a syrup. The unstable aldehyde was immediately used for next step.

Workup

  1. customThe reaction was quenched with addition of water
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe organic phase was washed successively with 1N hydrochloric acid, water and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a63bc6ff62534a929dfa3198dd730796
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211242B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes