HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-[(3-Chlorophenyl)ethynyl]-1,9,13-trioxa-2-azadispiro[4.2.5.2]pentadec-2-ene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 1,3-Propanediol | HCID 10442 | — |
| Reactant | 3-[(3-Chlorophenyl)ethynyl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-one | HCID 56646467 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | 3-[(3-Chlorophenyl)ethynyl]-1,9,13-trioxa-2-azadispiro[4.2.5.2]pentadec-2-ene | HCID 56644434 | 75.3% |
Reaction Steps
A solution of the compound of Example 32 (0.41 g, 1.42 mmol), 1,3-propandiol (0.15 g, 1.95 mmol) and p-toluensulfonic acid. H2O (7.5 mg, 0.04 mmol) in 30 mL of benzene was stirred at reflux for 10.5 h, removing water with a Dean-Stark Apparatus. Dilution with water, washing with aq. 5% NaHCO3, drying the organic layer over Na2SO4 afforded the title compound as dense yellow oil. This was further purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 7:3) giving a white solid. Yield: 75.3%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580962B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-d0bc22ea6457413e94f6946d7b902459 |
| Source note | uspto-grants-2013_11 |