Hydrochloric Acid → HCID 131730029, compound

Temperature

0 °C

26 (diethyl (2E)-4-oxopent-2-enamide) (5.92 g, 35 mmol) is dissolved in MeOH (14 ml) and H2O (56 ml) and cooled to 0° C. To the resulting solution is added NaBH4 (0.50 g, 13.1 mmol) in portions over 5 minutes. After 15 minutes of additional stirring at 0° C., the reaction mixture is acidified with 2 M HCl (30 ml) and extracted with AcOEt (1 l and 2×0.75 l). The organic phases are washed with H2O (100 ml), saturated NaHCO3 (100 ml) and brine (100 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. 27 (rac-Diethyl (2E)-4-hydroxypent-2-enamide) (5.66 g, 94%) is obtained as a pale yellow oil.

1. extractionextracted with AcOEt (1 l and 2×0.75 l)
2. washThe organic phases are washed with H2O (100 ml), saturated NaHCO3 (100 ml) and brine (100 ml) successively
3. dry with materialThe combined organic phases are dried with Na2SO4
4. customevaporated under reduced pressure at 40° C

ORD record

ord-c2758272aef041cc8dadb23f8f30ed94

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288566B2