Methyl propiolate → 2-[5-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]propanoic acid

HRID 887158Notes

Reaction equation

[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH:10]([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])=[N+:8]=[N-:9]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1]([C:2]1[N:7]([CH:10]([CH3:18])[C:11]([OH:13])=[O:12])[N:8]=[N:9][CH:3]=1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1.87 g (22.3 mmol) of methyl prop-2-ynoate in 40 mL of toluene was added 1.9 g (11 mmol) of tert-butyl 2-azidopropanate. The reaction mixture was heated at 100° C. for 3 h then cooled to ambient temperature. All volatiles were removed under reduced pressure and the crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient to afford the title compounds.

Workup

temperaturethen cooled to ambient temperature
customAll volatiles were removed under reduced pressure
customthe crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient

Sources & evidence

ORD record: ord-b40d0de4f7214028a1e188df026f7802
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247415B2

Reaction notes

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