Diisobutylaluminumhydride → HCID 90414955, compound

HRID 578823Notes

Reaction equation

HRID 578823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:17][CH3:18])=[N:10][C:11]([CH3:16])=[C:12]([CH:15]=2)[CH:13]=O)[CH:5]=[CH:6][CH:7]=1.[Cl:19]C1C=C(C2C(OC)=NC(C)=C(C=2)C#N)C=CC=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Cl:19][CH2:13][C:12]1[C:11]([CH3:16])=[N:10][C:9]([O:17][CH3:18])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 90414959HCID 90414959, compoundHCID 90414992HCID 90414992, compound

Product 1

HCID 90414955HCID 90414955, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-(3-Chlorophenyl)-6-methoxy-2-methylnicotinaldehyde. To a cooled solution, −78° C., of 5-(3-chlorophenyl)-6-methoxy-2-methylnicotinonitrile (500 mg, 1.9 mmol) in DCM (15 mL), under nitrogen, was added diisobutylaluminum hydride (1 M in hexanes, 4.8 mL, 4.8 mmol) drop-wise, over 3 minutes. The reaction mixture was stirred at −78° C. for 1 h. The reaction was carefully quenched by addition of saturated sodium fluoride (1 mL). After stirring for 30 minutes the suspension was filtered and the filtrate concentrated under reduced pressure. Purification (FCC, SiO2, 0-50%, EtOAc/hexanes) afforded the title compound (358 mg, 72%). [M+H]=262.05.

Workup

  1. customThe reaction was carefully quenched by addition of saturated sodium fluoride (1 mL)
  2. stirringAfter stirring for 30 minutes the suspension
  3. filtrationwas filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customPurification (FCC, SiO2, 0-50%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-c301df28e94743b4aa51aaf82bcc1bd3
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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