Isopropyl iodide → 5-Hydroxy-7-isopropoxy-2-methylthiochromone

HRID 2209661Notes

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>[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, 5 added to the solution thus reacted. The product was extracted twice with ethyl acetate. organic layer was washed with saturated salt water and dried over sodium sulfate anhydride. The solvent was distilled out under reduced pressure. The resulting crude product was purified by flash column cliromatography (hexane ethyl acetate =4:1), whereby 6.71 g of 5-hydroxy-7-isopropoxy-2-methylthiochromone was obtained (yield: 83%).

Workup

additionSubsequently, 5 added to the solution
customthus reacted
extractionThe product was extracted twice with ethyl acetate
washorganic layer was washed with saturated salt water
dry with materialdried over sodium sulfate anhydride
distillationThe solvent was distilled out under reduced pressure
customThe resulting crude product was purified by flash column cliromatography (hexane ethyl acetate =4:1)

Sources & evidence

ORD record: ord-02ee9af36fd8431e8b20c02648ac837f
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455267

Reaction notes

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