Propargyl alcohol → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HRID 58522

Reaction equation

[CH2:1]([OH:4])[C:2]#[CH:3].[N+:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-])=[O:6].C1N2CCN(CC2)C1>C(O)C>[OH:4][CH2:1][C:2]1[O:6][N:5]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of propargyl alcohol (1.0 mL; 16.76 mmol) and ethyl 2-nitroacetate (3.79 mL; 33.52 mmol) in ethanol (23.5 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.194 g; 1.68 mmol). The tube was heated at 80° C. for 72 h. After cooling, the mixture was evaporated to dryness and the residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to yield 2.32 g (81%) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil.

Workup

temperatureAfter cooling
customthe mixture was evaporated to dryness
customthe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

Sources & evidence

ORD record: ord-2f958587927640de86d953d3ffdfc723
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434722B2

Linked notes

Loading…