Diisobutylaluminum hydride → (2S)-2-(Benzyloxy)propanal

Temperature

-2.5 °C

A mixture of (S)-methyl 2-(benzyloxy)propanoate compound of formula-14 obtained in example-11 (100 g) and toluene (200 ml) was cooled to −75 to 70° C. under nitrogen atmosphere. DIBAL (500 ml) was added to the reaction mixture and stirred for 3 hours at the same temperature. After completion of the reaction, the reaction mixture was quenched with methanol and 30% hydrochloric acid was added to it at −75 to −70° C. Temperature of reaction mixture was raised to 25-30° C. Both organic and aqueous layers were separated and the aqueous layer was extracted with toluene. Both organic layers were combined, washed with 5% sodium bicarbonate and 10% sodium chloride solution. The organic layer containing title compound is carried for the next step without distillation.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched with methanol and 30% hydrochloric acid
3. additionwas added to it at −75 to −70° C
4. customTemperature of reaction mixture
5. temperaturewas raised to 25-30° C
6. customBoth organic and aqueous layers were separated
7. extractionthe aqueous layer was extracted with toluene
8. washwashed with 5% sodium bicarbonate and 10% sodium chloride solution
9. additionThe organic layer containing title compound
10. distillationis carried for the next step without distillation

ORD record

ord-74d12e583bbc4375bb2e9e38d79e193a

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102664B2