Pyridine → HCID 131730031, compound

27 (rac-Diethyl (2E)-4-hydroxypent-2-enamide) (1.05 g, 6.0 mmol), pyridine (969 μl, 12 mmol) and DMAP (147 mg, 0.60 mmol) are dissolved in toluene (30 ml) and THF (10 mL) and cooled to 0° C. Chloroacetylchloride (954 μl, 12 mol) in toluene (4 ml) is added dropwise under stirring at ≦2° C. over 15 min. The reaction mixture is stirred 2.5 h at 0° C. The resulting suspension is then poured onto H2O (50 ml) and extracted with tBuOMe (150 and 75 ml). The organic phases are washed with 1 M HCl (50 ml), H2O (50 ml), saturated NaHCO3 (50 ml) and brine (50 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is filtered with tBuOMe (50 ml) and tBuOMe:AcOEt 50:50 (300 ml) over SiO2 (15 g) and yields 34 (rac-Diethyl (2E)-4-(chloroacetoxy)pent-2-enamide) (1.46 g, 98%) as a yellow oil.

1. stirringThe reaction mixture is stirred 2.5 h at 0° C
2. additionThe resulting suspension is then poured onto H2O (50 ml)
3. extractionextracted with tBuOMe (150 and 75 ml)
4. washThe organic phases are washed with 1 M HCl (50 ml), H2O (50 ml), saturated NaHCO3 (50 ml) and brine (50 ml) successively
5. dry with materialThe combined organic phases are dried with Na2SO4
6. customevaporated under reduced pressure at 40° C
7. filtrationThe residue is filtered with tBuOMe (50 ml) and tBuOMe:AcOEt 50:50 (300 ml) over SiO2 (15 g)

ORD record

ord-94d44fe078c0404d9fcc7e5f2c41ee09

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288566B2