HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58248246, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | (-)-3-Hydroxytetrahydrofuran | HCID 641512 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58248246 | HCID 58248246 | 47% |
Reaction Steps
A solution of (R)-tetrahydrofuran-3-ol (1.1 g, 12.5 mmol) and triethylamine (13.6 mL, 97.5 mmol) in CH2Cl2 was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3×50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (R)-tetrahydrofuran-3-yl methanesulfonate (0.97 g, brown oil, 47% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08697709B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-5a2eac5b7d374a96a8b97786f00ac760 |
| Source note | uspto-grants-2014_04 |