Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sulfuryl chloride | HCID 24648 | — |
| Reactant | HCID 58281528 | HCID 58281528 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 44189333 | HCID 44189333 | 31.2% |
Reaction Steps
A dichloromethane (13 mL) solution of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonyl-5-methyl-2,5-dihydrothiophene (806 mg, 2.66 mmol) was cooled to −72° C., and to this solution, a dichloromethane (2.7 mL) solution of sulfuryl chloride (0.11 mL, 0.5 equivalent amount) was dropwise added over a period of 3 minutes. After the temperature of the solution was raised to room temperature, the solution was mixed with water (16 mL) and a saturated sodium chloride aqueous solution (16 mL), and extracted with dichloromethane. The dichloromethane solution was dried over a drying agent and purified by silica gel column chromatography (eluent: hexane/ethyl acetate=85/15 and then 4/1 (v/v)) to give the desired product as a yellow solid (0.25 g, yield: 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08642786B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-177222aeb3ef45d1a391d0e32f653585 |
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| Source note | uspto-grants-2014_02 |
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