Pyridine → HCID 131730030, compound

HRID 2065961Notes

Reaction equation

HRID 2065961 reaction equation
[CH2:1](/[C:3](=[CH:7]\[CH:8]([OH:10])[CH3:9])/[C:4]([NH2:6])=[O:5])[CH3:2].N1C=CC=CC=1.C1COCC1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.Cl>[CH2:1](/[C:3](=[CH:7]\[CH:8]([O:10][C:24](=[O:25])[CH2:23][Cl:22])[CH3:9])/[C:4]([NH2:6])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 131730028HCID 131730028, compound

Product 1

HCID 131730030HCID 131730030, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent2×

Procedure

25 (rac-Ethyl (2E)-4-hydroxypent-2-enamide) (886 mg, 6.0 mmol), pyridine (969 μl, 12 mmol) and DMAP (147 mg, 1.2 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 for 2.5 hours at 0° C. The resulting suspension is then poured in 2 M HCl (25 ml) and extracted with tBuOMe (250 and 150 ml). The organic phases are washed with 2 M HCl (25 ml), saturated NaHCO3 (15 ml) and brine (25 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. yielding 33 (rac-Ethyl (2E)-4-(chloroacetoxy)pent-2-enamide) (1.26 g, 95%) as a beige solid.

Workup

  1. stirringThe reaction mixture is stirred for 2.5 hours at 0° C
  2. extractionextracted with tBuOMe (250 and 150 ml)
  3. washThe organic phases are washed with 2 M HCl (25 ml), saturated NaHCO3 (15 ml) and brine (25 ml) successively
  4. dry with materialThe combined organic phases are dried with Na2SO4
  5. customevaporated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-6e94da49a9974a93b8143554b0d0b896
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

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