HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxygen → 4-(3-Dodecanoyloxypropyl)-5-hydroxy-2(5H)-furanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxygen | HCID 977 | — |
| Reactant | Rose Bengal Lactone | HCID 69439 | — |
| Reactant | 3-(2-Trimethylsilyl-4-furyl)propyl dodecanoate | HCID 15037127 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(3-Dodecanoyloxypropyl)-5-hydroxy-2(5H)-furanone | HCID 15037128 | — |
Reaction Steps
A mixture of 3-(5-trimethylsilyl-3-furyl)propyl dodecanoate (105 mg, 0.27 mmol) and Rose Bengal (5 mg) in tetrahydrofuran (6 ml) was exposed to singlet oxygen for 2.5 hours at -78 degrees. The residue, after solvent removal, was purified by preparative thin layer chromatography (TLC) (20×20 cm, 500 u silica plate; developed with 60% ethyl ether/petroleum ether). The title ester was obtained as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05322953 |
| Source dataset | uspto-grants-1994_06 |
| ORD ID | ord-10447f8850044a90b2e08a2950afd743 |
| Source note | uspto-grants-1994_06 |