HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cornforth reagent → (4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cornforth reagent | HCID 2724130 | — |
| Reactant | (1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol | HCID 57216772 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one | HCID 56998139 | 71% |
Reaction Steps
1.22 g (4.17 mmol) of (1S,4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol was dissolved in 36 ml of abs. CH2Cl2 and oxidized with 4.72 g (12.51 mmol) of pyridinium dichromate during 2 h at ambient temperature. Filtration overCelite, evaporation to dryness, and flash chromatography (SiO2, Hexane/AcOEt=7/3) produced 860 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-d25ec022b26f4318aa2de627382100bf |
| Source note | uspto-grants-1999_07 |