HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 3-(Benzyloxy)cyclobutane-1-sulfonyl chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Potassium 3-(benzyloxy)cyclobutane-1-sulfonate | HCID 86656336 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 3-(Benzyloxy)cyclobutane-1-sulfonyl chloride | HCID 58380535 | 38% |
Reaction Steps
POCl3 (0.34 mL, 3.558 mmol) was added to a cooled solution of potassium 3-(benzyloxy)cyclobutane-1-sulfonate (0.5 g, 1.779 mmol) in dry DCM (10 mL) at 0° C. This was followed by the slow addition of diisopropyl ethyl amine (0.65 mL, 3.558 mmol) and stirred the resulting reaction mixture at 0° C. for 2 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was extracted with DCM. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 0.15 g of the product (38% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466289B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-960729471ea94814b5bfa01cf023c0ef |
| Source note | uspto-grants-2013_06 |