Diisobutylaluminum hydride → HCID 58432110, compound

Temperature

-78 °C

To a solution of N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide (1.5 g, 5.1 mmol) in anhydr CH2Cl2 (12 mL) and anhydr toluene (6 mL) at −78° C. was added a solution of DIBALH (1 M in hexanes, 7.8 mL, 7.8 mmol) dropwise over 5 min. After stirring at −78° C. for 1 hr, the reaction was quenched with the dropwise addition of EtOAc. The mixture was stirred 2 min then Et2O and saturated aqueous NH4Cl were added and the mixture was warmed to room temp. After stirring for 30 min the mixture was diluted with EtOAc and H2O and the layers separated. 10% Aqueous potassium sodium tartrate was added to the aqueous layer and it was extracted with EtOAc/Et2O. The combined organics were washed with saturated aqeuous NH4Cl and dried over Na2SO4 to give 2-methoxy-2-(4-morpholinophenyl)acetaldehyde as a yellow oil (1.27 g). The product was used in the next synthetic step without further purification.

1. customthe reaction was quenched with the dropwise addition of EtOAc
2. stirringThe mixture was stirred 2 min
3. additionEt2O and saturated aqueous NH4Cl were added
4. temperaturethe mixture was warmed to room temp
5. stirringAfter stirring for 30 min the mixture
6. additionwas diluted with EtOAc and H2O
7. customthe layers separated
8. addition10% Aqueous potassium sodium tartrate was added to the aqueous layer and it
9. extractionwas extracted with EtOAc/Et2O
10. washThe combined organics were washed with saturated aqeuous NH4Cl
11. dry with materialdried over Na2SO4

ORD record

ord-7e4f45f5b1824fa1a93155e8ce82ae96

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102643B2