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

HRID 1488788Notes

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-ac85aeed44ce4a6b9c4927d126a5ec90
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05675023

Reaction notes

Loading…