HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (3aR,4R,5R,6aS)-Hexahydro-2-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-4-carboxaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 22842863 | HCID 22842863 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3aR,4R,5R,6aS)-Hexahydro-2-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-4-carboxaldehyde | HCID 11107879 | — |
Reaction Steps
A solution of Corey lactone, (1S,5R,6R,7R)-6-(hydroxymethyl)-7-(tetrahydropyranyioxy)-2-oxabicyclo[3.3.0]octan-3-one (1), (6.800 g) in dichloromethane (40 ml) was oxidized by means of Swern oxidetion with using a solution of oxalyl chloride (2M dichloromethan solution, 30 ml) in dichloromethane (100 ml), DMSO (8.45 ml), and triethylamine (16.9 ml). After the usual work up, Corey aldehyde, (1S,5R,6R,7R)-6-formyl-7-(tetrahydropyranyloxy)-2-oxabicyclo [3.3.0]octan-3-one (2) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05739161 |
| Source dataset | uspto-grants-1998_04 |
| ORD ID | ord-b1067328a6ac451e89f1dfb2a581d593 |
| Source note | uspto-grants-1998_04 |