Dabco → Ethyl 5-benzyl-4,5-dihydroisoxazole-3-carboxylate

HRID 58542

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[N+:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=[O:11].C1N2CCN(CC2)C1>C(O)C>[CH2:1]([CH:2]1[O:11][N:10]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of allylbenzene (0.73 mL; 5.39 mmol) and ethyl 2-nitroacetate (1.53 mL; 13.48 mmol) in ethanol (12 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.106 g; 0.92 mmol). The tube was heated at 80° C. for 60 h. The mixture was evaporated. The flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane) of the residue provided 1.06 g (85%) of ethyl 5-benzyl-4,5-dihydroisoxazole-3-carboxylate as an oil.

Workup

customThe mixture was evaporated

Sources & evidence

ORD record: ord-96d379e547be4c7abbefd27ba98a683b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434722B2

Linked notes

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