Ethylene carbonate → Methyl 4-(2-hydroxyethoxy)-3-(pyrrol-1-yl)benzoate

HRID 399834

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.O=C1O[CH2:21][CH2:20][O:19]1>[I-].C([N+](CC)(CC)CC)C.C(OCC)(=O)C.O1CCCC1>[OH:19][CH2:20][CH2:21][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1

Participants

Conditions

Temperature: 140 °C

Procedure

The mixture of methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate (1.5 g), 2-oxo-1,3-dioxolane (0.61 g) and tetraethylammonium iodide (0.38 g) was heated at 140° C. for 3 hours. The resultant mixture was dissolved in the solution of ethyl acetate and tetrahydrofuran. The solution was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave the residue, which was purified by column chromatography on silica gel eluting with the solution of chloroform and ethyl acetate (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 4-(2-hydroxyethoxy)-3-(pyrrol-1-yl)benzoate (1.25 g) as an oil.

Workup

washThe solution was washed with water
dry with materialdried over magnesium sulfate
customEvaporation of the solvent
customgave the residue, which
customwas purified by column chromatography on silica gel eluting with the solution of chloroform and ethyl acetate (9:1, V/V)
additionThe eluted fractions containing the desired product
customwere collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-0565baedab7543e2b053a14ace790971
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05824691

Linked notes

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