Diisobutylaluminumhydride → HCID 53915721, compound

HRID 373948Notes

Reaction equation

HRID 373948 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][O:22][C:23]1[CH:24]=[C:25]([CH:38]=[CH:39][CH:40]=1)[CH:26]=[CH:27][C:28]1[CH:37]=[CH:36][C:31]([C:32](OC)=[O:33])=[CH:30][CH:29]=1>CCCCCC.C1COCC1>[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][O:22][C:23]1[CH:24]=[C:25]([CH:38]=[CH:39][CH:40]=1)[CH:26]=[CH:27][C:28]1[CH:29]=[CH:30][C:31]([CH:32]=[O:33])=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 53866563HCID 53866563, compound

Product 1

HCID 53915721HCID 53915721, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisobutyl aluminum hydride (0.01 mol) in hexane is added dropwise to a solution of methyl 4-(3-(2-quinolinylmethyloxy)styryl)benzoate (0.01 mol) in 100 ml of THF at 0° C. The reaction mixture is stirred at 0° C. for 40 minutes and then quenched with methanol and Rochelle salt. Extraction with ethyl acetate and purified by column chromatography gives 4-(3-(2-quinolinylmethyloxy)styryl)benzaldehyde.

Workup

  1. customquenched with methanol and Rochelle salt
  2. extractionExtraction with ethyl acetate
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-5441c164381d4a13ba2eeeb77d7a407f
Source dataset
uspto-grants-1992_11
Patent number
US05166210

Reaction notes

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