Hydrochloric Acid → 7-Hydroxy-3-(2-hydroxyethyl)benzofuran

HRID 430747Notes

Reaction equation

[OH:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][C:12](OC)=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.O>C1COCC1>[OH:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][CH2:12][OH:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl (7-hydroxybenzofuran-3-yl)acetate (1.46 g) was dissolved in THF (30 ml) and the solution was cooled to 0° C. To this solution, lithium aluminum hydride (269 mg) was added and the solution was stirred for 3.5 hours. After making the pH of the reaction solution not more than 2 by adding 1N hydrochloric acid, the reaction solution was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). After combining the organic layers, the resultant was washed with saturated brine and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1) using silica gel to obtain the desired compound (1.09 g, yield: 86%).

Workup

extractionthe resultant was extracted twice with ethyl acetate (20 ml)
washthe resultant was washed with saturated brine
dry with materialdried over sodium sulfate
customAfter removing the sodium sulfate
filtrationby filtration
customthe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-72e681ff24be4ca680656c5c6e8b9a79
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323235B1

Reaction notes

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