Ethanol → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HRID 58533

Reaction equation

HRID 58533 reaction equation
[C:1]([CH:3]1CCCC1)#[CH:2].[N+:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:10])=O.C([OH:19])C>C1N2CCN(CC2)C1>[OH:19][CH2:3][C:1]1[O:10][N:8]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 69379Ethyl nitroacetateHCID 136725Cyclopentylacetylene

Product 1

HCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 9237DabcoCatalyst

Conditions

Temperature
80 °C

Procedure

To a mixture of ethynylcyclopentane (0.74 mL; 6.05 mmol) and ethyl 2-nitroacetate (1.37 mL; 12.11 mmol) in ethanol (9 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.070 g; 0.60 mmol). The tube was heated at 80° C. for 96 h. The mixture was evaporated. The flash chromatography on silica gel (eluent: 20 to 80% dichloromethane in heptane) of the residue provided 1.21 g (96%) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil.

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-3e064e2a2ad34f739bdcb8230f179c09
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

Loading…