Hydrochloric Acid → HCID 88021242, compound

Temperature

0 °C

(2E)-4-Oxopent-2-enoic acid (7.06 g, 60 mmol) and Et3N (8.7 ml, 63 mmol) are dissolved in CH2Cl2 (150 ml). The solution is cooled to 0° C. Then iBuOCOCl (8.8 ml, 67 mmol) in CH2Cl2 (10 ml) is added dropwise at ≦4° C. over 10 min. The resulting suspension is stirred for 25 min at 0° C. Et2NH (7.5 ml, 72 mmol) in CH2Cl2 (5 ml) is added dropwise over 10 min at ≦4° C. After 1.5 hours strung at 0° C., additional Et2NH (73.8 ml, 36 mmol) is added and stirring is continued for 3 hours. Then the reaction mixture is poured into 2 M HCl (100 ml) and extracted with TBME (750 ml and 2×250 ml). The organic phases are washed with 2 M HCl (100 ml), saturated NaHCO3 (100 and 50 ml) and brine (2×50 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is purified by flash chromatography (AcOEt:heptane fraction 50:50 to 60:40) and yields 26 (diethyl (2E)-4-oxopent-2-enamide) (7.16 g, 71%) as a pale orange oil.

1. waitAfter 1.5 hours strung at 0° C.
2. stirringstirring
3. waitis continued for 3 hours
4. extractionextracted with TBME (750 ml and 2×250 ml)
5. washThe organic phases are washed with 2 M HCl (100 ml), saturated NaHCO3 (100 and 50 ml) and brine (2×50 ml) successively
6. dry with materialThe combined organic phases are dried with Na2SO4
7. customevaporated under reduced pressure at 40° C
8. customThe residue is purified by flash chromatography (AcOEt:heptane fraction 50:50 to 60:40)

ORD record

ord-456c876a677046a1b38f51e43e22895e

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288566B2