HCID 14800776, compound → HCID 14800777, compound

HRID 729031Notes

Reaction equation

HRID 729031 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:37]=[CH:38][CH:39]=1)[CH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30](OC)=[O:31]>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:37]=[CH:38][CH:39]=1)[CH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[CH:30]=[O:31]

Participants

5

Reactant 2

HCID 14800776HCID 14800776, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14800777HCID 14800777, 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 3-(3-(2-quinolinylmethyloxy)benzyl)benzoate (0.01 mol) in 100 ml of THF at0° C. The reaction mixture is stirred at 0° C. for 30 minutesand then quenched with methanol and Rochelle salt. Extraction with ethyl acetate and purified by column chromatography gives 3-(3-(2-quinolinylmethyloxy)benzyl)benzaldehyde.

Workup

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

Sources & evidence

ORD record
ord-fcb037d114e84e4c88076d386d48a3a2
Source dataset
uspto-grants-1991_09
Patent number
US05051427

Reaction notes

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