Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Potassium hydroxy sulfite | HCID 23707502 | — |
| Reactant | HCID 68671175 | HCID 68671175 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68671607 | HCID 68671607 | 97.5% |
Reaction Steps
Ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-(8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl)acrylate (1.63 g, (E)/(Z)-mixture) was dissolved in methanol (16.3 mL)-THF (16.3 mL) mixed solvent, followed by ice-cooling. To this solution was added a solution of Oxone (registered trademark, 2.43 g) in water (16.3 mL), followed by warming to room temperature and stirring for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added thereto, and further added a 1 M aqueous sodium sulfite solution and ethyl acetate. The organic layer was separated and the aqueous layer was then extracted with ethyl acetate. The organic layer was further washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain ethyl 2-[3-bromo-4-(cyclopropylsulfinyl)phenyl]-3-(8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl)acrylate (1.64 g) as an (E)/(Z)-mixture of olefin.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08329707B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-23fb1c3b9c8d46d3b96c586fbfdcf0c0 |
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| Source note | uspto-grants-2012_12 |
|---|