Dimethylformamide → 5-Hydroxy-7-isopropoxy-2-methylthiochromone

HRID 1779523Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2.C(=O)([O-])[O-].[K+].[K+].[CH:21](I)([CH3:23])[CH3:22].CN(C=O)C>O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:21]([CH3:23])[CH3:22])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture consisting of 6.88 g (30.35 mmol) 5,7-dihydroxy-2-methylthiochromone, 12.56 g (91.05 mmol) potassium carbonate, 6.07 ml (60.70 mmol) isopropyl iodide, and 150 ml DMF was stirred at 60° C. for 30 min. Subsequently, water was added to the solution. The product was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled out under reduced pressure. The resulting crude product was purified by flash column chromatography (hexane ethyl acetate=4:1), whereby 6.71 g of 5-hydroxy-7-isopropoxy-2-methylthiochromone was obtained (yield: 83%).

Workup

extractionThe product was extracted twice with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled out under reduced pressure
customThe resulting crude product was purified by flash column chromatography (hexane ethyl acetate=4:1)

Sources & evidence

ORD record: ord-6f74120dd3b54cafa5108e45c7144b1d
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05627204

Reaction notes

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