Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | HCID 70896807 | HCID 70896807 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 70896830 | HCID 70896830 | 74% |
Reaction Steps
Triethylamine (2.9 mL, 20.7 mmol) and methanesulfonyl chloride (0.8 mL, 10.3 mmol) are added in the stated order to a solution of the allylic alcohol obtained in example (4) 1.b) (2.6 g, 6.9 mmol) in 1,2 dichloroethane (50 mL), cooled to 0° C. The reaction is monitored by thin layer chromatography (diethyl ether). The mixture is stirred at 0° C. until mesylate formation is complete, then maintained at room temperature until the product has completely formed. The solution is diluted with dichloromethane (50 mL) and washed with cold water, a 10% aqueous solution of cold hydrochloric acid, a saturated NaHCO3 solution, a saturated NaCl solution then dried over anhydrous Na2SO4. The solvent is removed under reduced pressure and the product purified by flash chromatography on a silica gel column using diethyl ether as eluant. 1.54 g (74%) of a white solid are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07691818B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-e085c6f3ff2e412b9fa54dc657bef592 |
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| Source note | uspto-grants-2010_04 |
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