HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Dimethyl (6-methyl-2-oxoheptyl)phosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Dimethyl (2-oxoheptyl)phosphonate | HCID 580181 | — |
| Reactant | (3aR,4S,5R,6aS)-(-)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one | HCID 2724453 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Dimethyl (6-methyl-2-oxoheptyl)phosphonate | HCID 15223968 | — |
Reaction Steps
To the suspension of sodium hydride (NaH) (60%, 250 mg) in THF (40 ml) was added dropwise dimethyl(2-oxoheptyl)phosphonate, and the reaction solution was stirred for 30 min. A THF solution (40 ml) of the aldehyde (2) previously prepared by Collins oxidization of (−)-Corey lactone (1) (2 g) was added. Reaction was maintained at room temperature overnight, and then acetic acid was added. After the usual work-up, an α,β-unsaturated ketone (3) was obtained. Yield: 1.95 g (50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06265440B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-e9c8e9dc483e4c37a0d75d2bdff3debb |
| Source note | uspto-grants-2001_07 |