Diisobutylaluminumhydride → HCID 90414955, compound

HRID 2271464Notes

Reaction equation

HRID 2271464 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 diisobutylaluminium 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-823475bbf00643dc82bd6a5e5226313e
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

Loading…