Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86691336 | HCID 86691336 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86691335 | HCID 86691335 | 74.1% |
Reaction Steps
4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentan-1-ol (59.1 mg, 0.275 mmol) and triethyl amine (835 mg, 8.25 mmol) were dissolved in anhydrous CH2Cl2 (20 mL), and then the solution was cooled to 0° C. p-toluenesulfonyl chloride (57.7 mg, 0.303 mmol) and DMAP (2.00 mg, 0.0138 mmol) were added thereto and the resulting solution was stirred at 0° C. for 6 hr. Water (30 mL) was added thereto to complete the reaction, extraction was performed by using CH2Cl2 (3×20 mL), an organic layer was washed with a brine solution, anhydrous magnesium sulfate was used to perform drying and distillation under reduced pressure, and then column chromatography was used to obtain 75.1 mg (yield 74%) of the title compound which is colorless and in the oil state.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08993766B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-9c1cca87891f45ec8ad5019bee698b17 |
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| Source note | uspto-grants-2015_03 |
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