Dabco → 2-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl ester

HRID 58537

Reaction equation

HRID 58537 reaction equation
[N+:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:3])=O.[CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[CH2:11].N12CCN(CC1)CC2>C(O)C>[C:12]1([CH:10]2[O:3][N:1]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:11]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 12757VinylcyclohexaneHCID 69379Ethyl nitroacetate

Product 1

HCID 5388222-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl esterYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-nitroacetate (0.96 mL; 8.70 mmol), vinylcyclohexane (0.6 mL; 4.35 mmol), 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.050 mg, 0.438 mmol) and ethanol (2 mL) was stirred at 80° C. for 60 hrs. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate 0.690 g (63%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-de5c93ef6ed34bc3937c7926e6f2a07d
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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