Ethyl 4-chloroacetoacetate → Ethyl 2-(2-cyclopropyloxazol-4-yl)acetate

HRID 1753083Notes

Reaction equation

HRID 1753083 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:11]1([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]1>C1(C)C=CC=CC=1.O1CCOCC1>[CH:11]1([C:14]2[O:15][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:16]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 80376Cyclopropanecarboxamide

Product 1

HCID 86672106Ethyl 2-(2-cyclopropyloxazol-4-yl)acetateYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl 4-chloroacetoacetate (20.0 g, 122.0 mmol) was added to cyclopropanecarboxamide (3.52 g, 41.5 mmol) in toluene (100 mL) and 1,4-dioxane (100 mL). The mixture was refluxed at 120° C. for 17 hours then evaporated in vacuo. The crude solid was purified by silica gel column chromatography eluting with 80:20 petroleum ether: EtOAc to afford the title compound as a white solid (50%, 4.00 g).

Workup

  1. customthen evaporated in vacuo
  2. customThe crude solid was purified by silica gel column chromatography
  3. washeluting with 80:20 petroleum ether

Sources & evidence

ORD record
ord-ef723420f05c47708b6109c3465c35e7
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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