Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Iodohexane | HCID 12527 | — |
| Reactant | HCID 10894986 | HCID 10894986 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18653280 | HCID 18653280 | — |
Reaction Steps
Potassium carbonate (500 mg, 3.6 mmol) and 1-iodohexane (1.0 ml, 6.79 mmol) were added to a solution of (S)-(E)-3-[1-(3,4-dihydroxy-5-methoxyphenyl)methyl]-2-(3,4,5-trimethoxybenzylidene)butanolide (324 mg, 0.78 mmol) in 10 ml of DMF, followed by stirring at 60° C. for 4.5 hours. The reaction mixture was poured into 50 ml of ethyl acetate and then the resulting solution was washed successively with water, 2N-HCl, water and saturated NaHCO3. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Brown oil thus obtained was purified by column chromatography (silica gel: "FUJI-DAVIDSON BW-300", eluent: 1:3 mixed solvent of ethyl acetate and hexane), whereby 310 mg of the title compound were obtained as colorless oil (yield: 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05321135 |
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| Source dataset | uspto-grants-1994_06 |
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| ORD ID | ord-3a9b2d034da1446bad02f3ae86938a84 |
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| Source note | uspto-grants-1994_06 |
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