Diisobutylaluminum hydride → HCID 58966966, compound

HRID 1948229Notes

Reaction equation

HRID 1948229 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:21](OC)=[O:22])[C:8]2=[O:25])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([CH2:21][OH:22])[C:8]2=[O:25])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69440473HCID 69440473, compound

Product 1

HCID 58966966HCID 58966966, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

According to Scheme 18: To a solution of methyl 1-(4-chlorobenzyl)-5-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (1 eq, 0.52 mmol, 0.20 g) in Et2O (7 mL) at −78° C. was added DIBAL (3 eq, 1.60 mmol, 1.11 g). The reaction was stirred at −78° C. for 30 minutes and 0° C. for 1 hour. The reaction was then allowed to warm to room temperature and quenched with saturated aqueous NH4Cl solution. The aqueous phase was extracted 3 times with AcOEt and the combined organic fractions were washed twice with water, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked 50 g column SiO2) using CH2Cl2/AcOEt 80/20 as eluent which was then recrystallized from pentane/Et2O to afford the title compound (0.04 mmol, 16.0 mg, 9%) as a beige solid.

Workup

  1. temperatureto warm to room temperature
  2. customquenched with saturated aqueous NH4Cl solution
  3. extractionThe aqueous phase was extracted 3 times with AcOEt
  4. washthe combined organic fractions were washed twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked 50 g column SiO2)
  9. customwas then recrystallized from pentane/Et2O

Sources & evidence

ORD record
ord-ed91145bfaca4ff5824da991491e3da8
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

Loading…