Water → 2-Methylindol-4-yloxyacetic acid allyl ester

HRID 11411Notes

Reaction equation

[CH3:1][CH:2]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].O>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([O:4][C:3](=[O:5])[CH:2]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:1])[CH:23]=[CH2:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-methylindol-4-yloxyacetic acid (2 g) in N,N-dimethylformamide (20 ml) was added anhydrous potassium carbonate (2.02 g) and allyl bromide (1.27 ml), and the mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added water and ethyl acetate, then separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give the title compound (1.88 g) having the following physical data.

Workup

customseparated
extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride, successively, dried
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate)

Sources & evidence

ORD record: ord-6a02d285179643be84a2f1e9dba40b37
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098234B2

Reaction notes

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