HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 3-Tetrahydropyranyloxy-8alpha-estra-1,3,5(10)-trien-17-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | (8α)-3-Hydroxyestra-1,3,5(10)-trien-17-one | HCID 9547221 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-Tetrahydropyranyloxy-8alpha-estra-1,3,5(10)-trien-17-one | HCID 15618136 | — |
Reaction Steps
A suspension of 2.0 g of 3-hydroxy-8a-estra-1,3,5(10)-trien-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 15 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.3 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 2.2 g of 3-tetrahydropyranyloxy-8a-estra-1,3,5(10)-trien-17-one is obtained as colorless crystals with a melting point of 153-155° C., [α]D22 =+47.5° (c=0.53% in pyridine).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06136800 |
| Source dataset | uspto-grants-2000_10 |
| ORD ID | ord-dbbd6ce2084c405784513d116580301b |
| Source note | uspto-grants-2000_10 |