HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cornforth reagent → (4aS,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cornforth reagent | HCID 2724130 | — |
| Reactant | (1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol | HCID 86754179 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4aS,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one | HCID 57031123 | 76.2% |
Reaction Steps
590 mg (2.03 mmol) of (1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol was dissolved in 10 ml of abs. CH2Cl2 and oxidized with 1.91 g (5.08 mmol) of pyridinium dichromate during 2 h at ambient temperature. Filtration over Celite, evaporation to dryness, and flash chromatography (SiO2, Hexane/AcOEt=7/3) produced 446 mg of the title compound as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05919986 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-801ee2425ab64c68a676b37cdd669972 |
| Source note | uspto-grants-1999_07 |